3-phenoxy-4-pyridazinol derivatives and herbicide composition containing the same

ABSTRACT

A compound represented by the formula: 
                         
[wherein R 1  represents a hydrogen atom, a halogen, atom, alkyl group, etc.,
         R 2  represents a hydrogen atom, a halogen atom, alkyl group, etc.,   R 3 , R 4 , R 5 , R 6  and R 7  each independently represent a hydrogen atom, a halogen atom, a substitutable alkyl group, a substitutable alkenyl group, alkynyl group, a substituteable cycloalkyl group, etc., or R 3 , R 4 , R 5 , R 6  and R 7  may form a ring which may be substituted, which is formed by the adjacent two of them with carbon atoms to which the respective substituents are bonded,   m and n each independently represent 0 or 1.] a salt thereof, an ester derivative thereof and an agricultural chemical containing the same as an effective ingredient, and a herbicidal composition containing the compound and a second herbicidally active compound as effective ingredients.

This application is the United States national phase application ofInternational Application PCT/JP02/08278 filed Aug. 14, 2002.

TECHNICAL FIELD

The present invention relates to a 3-phenoxy-4-pyridazinol compound, itssalt, its ester derivative and agricultural chemical containing the sameas an effective ingredient, and a herbicidal composition containing3-phenoxy-4-pyridazinol compound and a second herbicidally activecompound as effective ingredients.

BACKGROUND ART

In Chemical Pharmaceutical Bulletin, 1972, vol. 20, No. 10, pp.2191-2203, 3-(2-allylphenoxy)-6-chloro-4-methoxypyridazine has beendisclosed but a 3-phenoxy-4-pyridazinol compound having a hydroxyl groupat the 4-position of the pyridazine has not been disclosed, and there isno description about a herbicide.

In Journal of the Chemical Society: Perkin Transaction I, 1975, No. 6,pp. 534-538, 3-(2-hydroxyphenoxy)-4-methoxypyridazine and6-chloro-3-(2-hydroxyphenoxy)-4-methoxypyridazine has been disclosed buta 3-phenoxy-4-pyridazinol compound having a hydroxyl group at the4-position of the pyridazine has not been disclosed, and there is nodescription about a herbicide.

In U.S. Pat. No. 5,559,080, a 3-(phenoxy which may besubstituted)pyridazine compound having a haloalkylphenoxy group at the4-position of the pyridazine has been disclosed but a3-phenoxy-4-pyridazinol compound having a hydroxyl group at the4-position of the pyridazine has not been disclosed. Also, in the3-(phenoxy which may be substituted)pyridazine compound having ahaloalkylphenoxy group at the 4-position of the pyridazine, an oxygenatom bonded to the 4-position of the pyridazine is bonded by a benzenering, and its herbicidal activity was insufficient.

Also, at present, a number of herbicides have been practically used as aherbicide for a paddy field, and widely been used for general purpose asa single agent and a mixed agent. However, there are many kinds of paddyfield weeds, and germination and growth period of the respective weedsare not uniform, in particular, occurrence of perennial weeds ranges fora long period of time. Thus, it is extremely difficult to prevent fromand kill all weeds with one time spread of a herbicide. Accordingly, asa herbicide, an appearance of a chemical which can kill many kinds ofweeds including annual weeds and perennial weeds, that is, which has awide weed-killing spectrum, is effective for already grown weeds,preventing and killing effects of weeds of which can be maintained for acertain period of time, and has high safety to paddy rice has earnestlybeen desired.

Also, as upland herbicides, a number of herbicides have now beencommercially available and practically used, but there are many kinds ofweeds to be prevented, and occurrence thereof ranges for a long periodof time, so that a herbicide which has higher herbicidal effects, hasbroad weed-killing spectrum, and causes no chemical damage to crops hasbeen desired.

One of the effective ingredient of the herbicidal composition of thepresent invention (hereinafter referred to as a second herbicidallyactive compound),4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate[hereinafter referred to as Compound A. General name: Pyrazolate],2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone[hereinafter referred to as Compound B. General name: Pyrazoxyfen],2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-4′-methylacetophenone[hereinafter referred to as Compound C. General name: Benzofenap],5-cyclopropyl-1,2-oxazol-4-yl α,α,α-trifluoro-2-mesyl-p-tolyl ketone[hereinafter referred to as Compound D. General name: Isoxaflutole],2-(2-chloro-4-mesylbenzoyl)cyclohexan-1,3-dione [hereinafter referred toas Compound E. General name: sulcotrione],2-(4-mesyl-2-nitrobenzoyl)cyclohexan-1,3-dione [hereinafter referred toas Compound F. General name: mesotrion] and4-chloro-2-(methylsulfonyl)phenyl 5-cyclopropyl-4-isoxazolyl ketone[hereinafter referred to as Compound G. General name: Isoxachlortole]are each conventionally known herbicidal compound, and each described inThe Pesticide Manual 11th Edition, pp. 1049 to 1050, Ibid. pp. 1054 to1055, Ibid. pp. 111 to 112, The Pesticide Manual, 12th Edition p. 563,Ibid. p. 848, Ibid. p. 602 and EP 470 856(1990). These compounds havehigh effects against annual broad-leaved weeds and a part of perennialweeds, but their effects against rice plant weeds or a part of perennialweeds are not necessarily sufficient.

DISCLOSURE OF THE INVENTION

The present inventors have earnestly studied about pyridazinederivatives having a phenoxy group at the 3-position thereof, and as aresult, they have found that a compound having a hydroxyl group at the4-position of the pyridazine ring shows substantially no chemical damageagainst paddy rice, and shows excellent herbicidal activity against awide range of weeds in a paddy field with a low dosage to accomplish thepresent invention. Moreover, they have found that similar herbicidalactivities are possessed by an ester derivative thereof in which abonding between an oxygen atom at the 4-position of the pyridazine ringand an acyl group is cleaved in a soil or in a plant body to beconverted into a compound in which a hydrogen atom binds to the oxygenatom, whereby accomplished the present invention.

Also, the present inventors have continued to search on a herbicidewhich can completely prevent and remove various kinds of weeds with onetime spread, has extremely high safety to paddy rice or upland crops,and has extremely low toxicity against humans and animals for thepurpose of overcoming the above-mentioned problems involved in theconventional herbicides such as second herbicidally active compounds A,B, C, D, E, F and G, and as a result, they have found that byformulating the above-mentioned 3-phenoxy-4-pyridazinol derivatives andthe second herbicidally active compound as effective ingredients, aweed-killing spectrum can be enlarged, and serious weeds can beprevented and killed with a smaller amount of effective ingredients bytheir synergistic action, whereby accomplished the present invention.

The present invention relates to a compound represented by the formula:

[wherein R¹ represents a hydrogen atom, a halogen atom, a C₁ to C₆ alkylgroup, a C₁ to C₆ haloalkyl group, a C₃ to C₆ cycloalkyl group, a C₂ toC₆ alkenyl group, a cyano group, a C₂ to C₇ alkylcarbonyl group, a di(C₁to C₆ alkyl)carbamoyl group, a phenyl group which may be substituted(The substituent is a substituent selected from the followingsubstituent Group A.), a 5 or 6-membered heterocyclic group (theheterocycle contains one nitrogen atom, oxygen atom or sulfur atom inthe ring, and may contain further 1 or 2 nitrogen atom(s).), a C₁ to C₆alkoxy group, a phenoxy group which may be substituted (The substituentis a substituent selected from the following substituent Group A.) or a5- or 6-membered heterocycloxy group which may be substituted {theheterocycle contains one nitrogen atom, oxygen atom or sulfur atom inthe ring, and may contain further 1 or 2 nitrogen atom(s). Thesubstituent is a substituent(s) selected from the group consisting of abenzoyl group which may be substituted (The substituent is a substituentselected from the following substituent Group A.) and a C₁ to C₆ alkylgroup.},

R² represents a hydrogen atom, a halogen atom, a C₁ to C₆ alkyl group, a(C₁ to C₆ alkoxy)C₁ to C₆ alkyl group, a benzoyl group which may besubstituted (The substituent is a substituent selected from thefollowing substituent Group A.), a C₂ to C₇ alkoxycarbonyl group, aphenoxy group which may be substituted (The substituent is a substituentselected from the following substituent Group A.), a phenylthio groupwhich may be substituted (The substituent is a substituent selected fromthe following substituent Group A.) or a tri(C₁ to C₆ alkyl)silyl group,

R³, R⁴, R⁵, R⁶ and R⁷ each independently represent a hydrogen atom, ahalogen atom, a C₁ to C₆ alkyl group which may be substituted (Thesubstituent is a substituent selected from the following substituentGroup B.), a C₂ to C₆ alkenyl group which may be substituted (Thesubstituent is a cyano group or a nitro group.), a C₂ to C₆ alkynylgroup, a C₃ to C₆ cycloalkyl group which may be substituted (Thesubstituent is a substituent selected from the following substituentGroup C.), a C₄ to C₁₀ bicycloalkyl group, a cyano group, a formylgroup, a C₂ to C₇ alkylcarbonyl group, a benzoyl group which may besubstituted (The substituent is a substituent selected from thefollowing substituent Group A.), a carboxyl group, a C₂ to C₇alkoxycarbonyl group, a carbamoyl group, a di(C₁ to C₆ alkyl)-carbamoylgroup, a phenyl group which may be substituted (The substituent is asubstituent selected from the following substituent Group A.), a 3- to6-membered heterocyclic group which may be substituted (the heterocyclecontains one nitrogen atom, oxygen atom or sulfur atom in the ring, andmay contain further 1 or 2 nitrogen atom(s), or may be fused with abenzene ring. The substituent is a substituent selected from thefollowing substituent Group E.), an amino group which may be substituted(The substituent is a substituent selected from the followingsubstituent Group D.), a nitro group, a hydroxyl group, a C₁ to C₆alkoxy group, a C₁ to C₆ haloalkoxy group, a (C₁ to C₆ alkoxy)C₁ to C₆alkoxy group, a phenoxy group which may be substituted (The substituentis a hydroxyl group or a pyridazinyloxy group substituted by asubstituent(s) selected from the group consisting of a halogen atom anda C₁ to C₆ alkoxy group.), a 5- to 6-membered heterocycloxy group whichmay be substituted (the heterocycle contains one nitrogen atom, oxygenatom or sulfur atom in the ring, and may contain further 1 or 2 nitrogenatom(s). The substituent is a substituent selected from the followingsubstituent Group E.), a phenylsulfonyloxy group which may besubstituted (The substituent is a substituent selected from thefollowing substituent Group A.), a C₁ to C₆ alkylthio group, a C₁ to C₆alkylsulfinyl group, a C₁ to C₆ alkylsulfonyl group or a tri(C₁ to C₆alkyl)silyl group, or R³, R⁴, R⁵, R⁶ and R⁷ may form a 3- to 6-memberedcyclic hydrocarbon group which may be substituted, which is formed bythe adjacent two of them with carbon atoms to which the respectivesubstituents are bonded (the cyclic hydrocarbon may be interrupted bythe same or different 1 to 2 hetero atom(s) selected from the groupconsisting of a nitrogen atom, an oxygen atom and a sulfur atom. Thesubstituent is a halogen atom, a C₁ to C₆ alkyl group, a hydroxy-C₁ toC₆ alkyl group, a C₁ to C₆ alkoxy group, an oxo group, a hydroxyiminogroup or a C₁ to C₆ alkoxyimino group, and when the C₁ to C₆ alkyl groupis substituted, it may form another 3-membered ring by combining, withthe other C₁ to C₆ alkyl group or a carbon atom(s) in the cyclichydrocarbon.),

m and n each independently represent 0 or 1,

the substituent Group A is a group selected from the group consisting ofa halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, a C₃to C₆ cycloalkyl group, a cyano group and a tri(C₁ to C₆ alkyl)silylgroup,

the substituent Group B is a group selected from the group consisting ofa halogen atom, a C₃ to C₆ cycloalkyl group, a cyano group, a C₂ to C₇alkylcarbonyl group, a C₂ to C₇ alkoxycarbonyl group, a phenyl group, aC₁ to C₆ alkoxy group, a C₁ to C₆ alkylthio group, a C₁ to C₆alkylsulfinyl group, a C₁ to C₆ alkylsulfonyl group, a C₁ to C₄alkylenedioxy group, a hydroxyimino group and a C₁ to C₆ alkoxyiminogroup,

the substituent Group C is a group selected from the group consisting ofa halogen atom, a C₁ to C₆ alkyl group which may be substituted (Thesubstituent is a substituent selected from the above-mentionedsubstituent Group B.), a C₃ to C₆ cycloalkyl group, a C₂ to C₆ alkenylgroup, a cyano group, a C₂ to C₇ alkylcarbonyl group, a benzoyl group, acarboxyl group, a C₂ to C₇ alkoxycarbonyl group, a carbamoyl group, adi(C₁ to C₆ alkyl)carbamoyl group, a phenyl group which may besubstituted (The substituent is a substituent selected from theabove-mentioned substituent Group A.), a 5 or 6-membered heterocyclicgroup (the heterocycle contains one nitrogen atom, oxygen atom or sulfuratom in the ring, and may contain further 1 or 2 nitrogen atom(s).), anamino group which may be substituted (The substituent is a substituentselected from the following substituent Group D.), a nitro group, ahydroxyl group, a C₁ to C₆ alkoxy group, a C₁ to C₆ haloalkoxy group, aphenoxy group, a C₁ to C₆ alkylthio group, a phenylthio group, a C₁ toC₆ alkylsulfinyl group and a C₁ to C₆ alkylsulfonyl group,

the substituent Group D is a group selected from the group consisting ofa C₁ to C₆ alkyl group, a C₂ to C₇ alkylcarbonyl group, a C₂ to C₇alkoxycarbonyl group, a di(C₁ to C₆ alkyl)carbamoyl group and a C₁ to C₆alkylsulfonyl group,

the substituent Group E is a group selected from the group consisting ofa halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₆ haloalkyl group, ahydroxyl group, a phenylsulfonyl group which may be substituted (Thesubstituent is a substituent selected from the above-mentionedsubstituent Group A.) and a di(C₁ to C₆ alkyl)sulfamoyl group.], itssalt or its ester derivative, an agricultural chemical containing thesame as an effective ingredient, and, a herbicidal compositioncontaining one or more 3-phenoxy-4-pyridazinol derivatives selected fromthe group consisting of the above-mentioned compounds, their salt andtheir ester derivatives, and one or more second herbicidally activecompound selected from the group consisting of

4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate,2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone,2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-4′-methylacetophenone,5-cyclopropyl-1,2-oxazol-4-yl α,α,α-trifluoro-2-mesyl-p-tolyl ketone,2-(2-chloro-4-mesylbenzoyl)cyclohexan-1,3-dione,2-(4-mesyl-2-nitrobenzoyl)cyclohexan-1,3-dione and4-chloro-2-(methylsulfonyl)phenyl 5-cyclopropyl-4-isoxazolyl ketone aseffective ingredients.

In the present invention, “a halogen atom” is a fluorine atom, achlorine atom, a bromine atom or an iodine atom, preferably a fluorineatom, a chlorine atom or a bromine atom, more preferably a chlorine atomor a bromine atom, still further preferably a chlorine atom.

In the present invention, the “C₁ to C₆ alkyl group” is a straight orbranched alkyl group having 1 to 6 carbon atoms, for example, it may bemethyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl, t-butyl,pentyl, isopentyl, 2-methylbutyl, neopentyl, 1-ethylpropyl, hexyl,4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl,3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl,1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl or 2-ethylbutylgroup, preferably a straight or branched alkyl group having 1 to 4carbon atoms (a C₁ to C₄ alkyl group), more preferably a straight orbranched alkyl group having 1 to 3 carbon atoms (a C₁ to C₃ alkylgroup), still further preferably an alkyl group having 1 to 2 carbonatoms (a C₁ to C₂ alkyl group), particularly preferably a methyl group.

In the present invention, the “C₁ to C₆ haloalkyl group” is the “C₁ toC₆ alkyl group” to which the same or different above-mentioned 1 to 5 “ahalogen atom(s)” is/are substituted, and for example, it may bechloromethyl, dichloromethyl, trichloromethyl, 1-chloroethyl,2-chloroethyl, 2,2,2-trichloroethyl, 1-chloropropyl, 3-chloropropyl,1-chlorobutyl, 4-chlorobutyl, fluoromethyl, difluoromethyl,trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2,2-trifluoroethyl,pentafluoroethyl, fluorochloromethyl, bromomethyl, 1-bromoethyl,2-bromoethyl or iodomethyl group, preferably a C₁ to C₃ alkyl groupsubstituted by the same or different 1 to 3 substituent(s) selected fromthe group consisting of a fluorine atom, a chlorine atom and a bromineatom, more preferably a C₁ to C₂ alkyl group substituted by the same 1to 3 fluorine atom(s) or chlorine atom(s), still further preferably afluoromethyl, difluoromethyl, trifluoromethyl or 2,2,2-trichloroethylgroup, particularly preferably a trifluoromethyl group.

In the present invention, the “C₃ to C₆ cycloalkyl group” is acyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl group, preferablycyclopropyl or cyclobutyl group, more preferably cyclopropyl group.

In the present invention, the “C₂ to C₆ alkenyl group” is a straight orbranched alkenyl group having 2 to 6 carbon atoms, for example, it maybe vinyl, 1-methylvinyl, 1-propenyl, 1-methyl-1-propenyl, 2-propenyl,1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-ethyl-2-propenyl, 2-butenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-ethyl-2-butenyl, 3-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 1-ethyl-3-butenyl, 2-pentenyl,1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 4-pentenyl,1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 2-hexenyl, 3-hexenyl,4-hexenyl or 5-hexenyl group, preferably a straight or branched alkenylgroup having 2 to 4 carbon atoms (a C₂ to C₄ alkenyl group), morepreferably a vinyl, 1-methylvinyl, 2-propenyl or 1-methyl-2-propenylgroup.

In the present invention, the “C₂ to C₇ alkylcarbonyl group” is acarbonyl group to which the above-mentioned “C₁ to C₆ alkyl group” isbonded, and for example, it may be an acetyl, propionyl, butyryl,isobutyryl, valeryl, isovaleryl, pivaloyl, hexanoyl or heptanoyl group,preferably a carbonyl group to which a straight or branched alkyl grouphaving 1 to 4 carbon atoms is bonded (a C₂ to C₅ alkylcarbonyl group),still further preferably a carbonyl group to which a straight orbranched alkyl group having 1 to 3 carbon atoms is bonded (a C₂ to C₄alkylcarbonyl group), particularly preferably an acetyl, propionyl,valeryl or pivaloyl group, most preferably an acetyl group.

In the present invention, the “di(C₁ to C₆ alkyl)-carbamoyl group” is acarbamoyl group in which the same or different two above-mentioned “C₁to C₆ alkyl groups” are bonded to a nitrogen atom, and for example, itmay be a dimethylcarbamoyl, methylethylcarbamoyl, diethylcarbamoyl,dipropylcarbamoyl, dibutylcarbamoyl or dihexylcarbamoyl group,preferably a carbamoyl group in which the same two straight or branchedalkyl groups having 1 to 3 carbon atoms are bonded {a di(C₁ to C₃alkyl)carbamoyl group}, more preferably a dimethylcarbamoyl group or adiethylcarbamoyl group, still further preferably a dimethylcarbamoylgroup.

In the present invention, the “tri(C₁ to C₆ alkyl)-silyl group” is asilicon atom to which the same or different three above-mentioned “C₁ toC₆ alkyl groups” are bonded, and for example, it may be atrimethylsilyl, triethylsilyl, triisopropylsilyl,dimethylisopropylsilyl, t-butyldimethylsilyl or trihexylsilyl group,preferably a silicon atom to which the same or different three straightor branched alkyl groups having 1 to 3 carbon atoms are bonded {a tri(C₁to C₃ alkyl)silyl group}, more preferably a trimethylsilyl ordimethylisopropylsilyl group, still further preferably a trimethylsilylgroup.

In the present invention, “a phenyl group which may be substituted (Thesubstituent is a substituent selected from the substituent Group A.)” isa phenyl group which may be substituted by the same or different 1 to 5substituent(s) selected from the group consisting of the above-mentioned“halogen atom”, the above-mentioned “C₁ to C₆ alkyl group”, theabove-mentioned “C₁ to C₆ haloalkyl group”, the above-mentioned “C₃ toC₆ cycloalkyl group”, a cyano group and the above-mentioned “tri(C₁ toC₆ alkyl)-silyl group”, and for example, it may be a phenyl,fluorophenyl, difluorophenyl, trifluorophenyl, chlorophenyl,dichlorophenyl, trichlorophenyl, fluorochlorophenyl, methylphenyl,dimethylphenyl, trimethylphenyl, tetramethylphenyl, pentamethylphenyl,ethylphenyl, fluoro(methyl)phenyl, chloro(methyl)phenyl,bromo(methyl)phenyl, cyclopropylphenyl, cyclopropyl(fluoro)phenyl,chloro(cyclopropyl)phenyl, cyclopropyl(methyl)phenyl,(trifluoromethyl)phenyl or fluoro(trifluoromethyl)phenyl group,preferably a phenyl group which may be substituted by the same ordifferent 1 to 3 substituent(s) selected from the group consisting of afluorine atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group,“a C₁ to C₃ alkyl group substituted by the same or different 1 to 3substituent(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom”, a C₃ to C₄ cycloalkyl group, a cyanogroup and a tri(C₁ to C₃ alkyl)silyl group, more preferably a phenyl,chlorophenyl, methylphenyl, trifluorophenyl or cyanophenyl group.

In the present invention, the “5 or 6-membered heterocyclic group (theheterocycle contains one nitrogen atom, oxygen atom or sulfur atom inthe ring, and may contain further 1 or 2 nitrogen atom(s).)” is a 5- to6-membered heterocyclic group which contains one nitrogen atom, oxygenatom or sulfur atom as a hetero atom and may further contain 1 to 2nitrogen atom(s), and for example, it may be a furyl, thienyl, pyrrolyl,pyrazolyl, imidazolyl, isoxazolyl, oxazolyl, isothiazolyl, thiazolyl,triazolyl, pyranyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl ortriazinyl group, preferably a 5-membered heterocyclic group (theheterocycle contains one nitrogen atom, oxygen atom or sulfur atom inthe ring.), more preferably a furyl or thienyl group.

In the present invention, the “C₁ to C₆ alkoxy group” is a straight orbranched alkoxy group having 1 to 6 carbon atoms, and for example, itmay be a methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy,s-butoxy, t-butoxy, pentoxy, isopentoxy, 2-methylbutoxy, neopentoxy,1-ethylpropoxy, hexyloxy, 4-methylpentoxy, 3-methylpentoxy,2-methylpentoxy, 1-methylpentoxy, 3,3-dimethylbutoxy,2,2-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy,1,3-dimethylbutoxy, 2,3-dimethylbutoxy or 2-ethylbutoxy group,preferably a straight or branched alkoxy group having 1 to 3 carbonatoms (a C₁ to C₃ alkoxy group), more preferably a methoxy or ethoxygroup, still further preferably a methoxy group.

In the present invention, the “phenoxy group which may be substituted(The substituent is a substituent selected from the substituent GroupA.)” is a phenoxy group which may be substituted by the same ordifferent 1 to 5 substituent(s) selected from the group consisting ofthe above-mentioned “halogen atom”, the above-mentioned “C₁ to C₆ alkylgroup”, the above-mentioned “C₁ to C₆ haloalkyl group”, theabove-mentioned “C₃ to C₆ cycloalkyl group”, a cyano group and theabove-mentioned “tri(C₁ to C₆ alkyl)-silyl group”, and for example, itmay be a phenoxy, fluorophenoxy, difluorophenoxy, trifluorophenoxy,chlorophenoxy, dichlorophenoxy, trichlorophenoxy, fluorochlorophenoxy,methylphenoxy, dimethylphenoxy, trimethylphenoxy, tetramethylphenoxy,pentamethylphenoxy, ethylphenoxy, fluoro(methyl)phenoxy,chloro(methyl)phenoxy, bromo(methyl)phenoxy, cyclopropylphenoxy,cyclopropyl(fluoro)phenoxy, chloro(cyclopropyl)phenoxy,cyclopropyl(methyl)phenoxy, (trifluoromethyl)phenoxy orfluoro(trifluoromethyl)phenoxy group, preferably a phenoxy group whichmay be substituted by the same or different 1 to 3 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atom,a bromine atom, a C₁ to C₃ alkyl group, “a C₁ to C₃ alkyl groupsubstituted by the same or different 1 to 3 substituent(s) selected fromthe group consisting of a fluorine atom, a chlorine atom and a bromineatom”, a C₃ to C₄ cycloalkyl group, a cyano group and a tri(C₁ to C₃alkyl)silyl group, more preferably a phenoxy, chlorophenoxy,methylphenoxy, trifluorophenoxy or cyanophenoxy group.

In the present invention, “a benzoyl group which may be substituted (Thesubstituent is a substituent selected from the substituent Group A.)” isa benzoyl group which may be substituted by the same or different 1 to 5substituent(s) selected from the group consisting of the above-mentioned“halogen atom”, the above-mentioned “C₁ to C₆ alkyl group”, theabove-mentioned “C₁ to C₆ haloalkyl group”, the above-mentioned “C₃ toC₆ cycloalkyl group”, a cyano group and the above-mentioned “tri(C₁ toC₆ alkyl)silyl group”, and for example, it may be a benzoyl,fluorobenzoyl, difluorobenzoyl, trifluorobenzoyl, chlorobenzoyl,dichlorobenzoyl, trichlorobenzoyl, fluorochlorobenzoyl, methylbenzoyl,dimethylbenzoyl, trimethylbenzoyl, tetramethylbenzoyl,pentamethylbenzoyl, ethylbenzoyl, fluoro(methyl)benzoyl,chloro(methyl)benzoyl, bromo(methyl)benzoyl, cyclopropylbenzoyl,cyclopropyl(fluoro)benzoyl, chloro(cyclopropyl)benzoyl,cyclopropyl(methyl)benzoyl, (trifluoromethyl)benzoyl orfluoro(trifluoromethyl)benzoyl group, preferably a benzoyl group whichmay be substituted by the same or different 1 to 3 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atom,a bromine atom, a C₁ to C₃ alkyl group, “a C₁ to C₃ alkyl group whichmay be substituted by the same or different 1 to 3 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atomand a bromine atom”, a C₃ to C₄ cycloalkyl group, a cyano group and atri(C₁ to C₃ alkyl)silyl group, more preferably a benzoyl,chlorobenzoyl, dichlorobenzoyl, methylbenzoyl, trifluorobenzoyl orcyanobenzoyl group.

In the present invention, “the 5- or 6-membered heterocycloxy groupwhich may be substituted {the heterocycle contains one nitrogen atom,oxygen atom or sulfur atom in the ring, and may contain further 1 or 2nitrogen atom(s). The substituent may be substituted by a substituent(s)selected from the group consisting of a benzoyl group which may besubstituted (The substituent is a substituent selected from thesubstituent Group A.) and a C₁ to C₆ alkyl group.}” is “a 5- to6-membered heterocycloxy group which contains one nitrogen atom, oxygenatom or sulfur atom as a hetero atom, and may contain further 1 or 2nitrogen atom(s)” which may be substituted by the same or different 1 to3 substituent(s) selected from the group consisting of theabove-mentioned “a benzoyl group which may be substituted (Thesubstituent is a substituent selected from the substituent Group A.)”and the above-mentioned “C₁ to C₆ alkyl group”, preferably a benzoylgroup which may be substituted by the same or different 1 to 3substituent(s) selected from the group consisting of a fluorine atom, achlorine atom, a bromine atom, a C₁ to C₃ alkyl group, “a C₁ to C₃ alkylgroup substituted by the same or different 1 to 3 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atomand a bromine atom”, a C₃ to C₄ cycloalkyl group, a cyano group and atri(C₁ to C₃ alkyl)silyl group, and “a 5-membered heterocycloxy groupwhich contains one nitrogen atom, oxygen atom or sulfur atom as a heteroatom, and which may contain further one nitrogen atom” substituted bythe same two C₁ to C₃ alkyl groups, more preferably a benzoyl groupsubstituted by two chlorine atoms and a pyrazolyloxy group substitutedby two C₁ to C₂ alkyl groups.

In the present invention, “the (C₁ to C₆ alkoxy)-C₁ to C₆ alkyl group”is the above-mentioned “C₁ to C₆ alkyl group” substituted by one of theabove-mentioned “C₁ to C₆ alkoxy groups”, and for example, it may be amethoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl,s-butoxymethyl, t-butoxymethyl, pentyloxymethyl, hexyloxymethyl,methoxyethyl, ethoxyethyl, propoxyethyl, butoxyethyl, methoxypropyl,methoxybutyl, methoxypentyl or methoxyhexyl group, preferably a C₁ to C₆alkyl group substituted by one C₁ to C₃ alkoxy group, more preferably amethoxyethyl, ethoxyethyl or ethoxymethyl group.

In the present invention, “C₂ to C₇ alkoxycarbonyl group” is a carbonylgroup to which the above-mentioned “C₁ to C₆ alkoxy group” is bonded,and for example, it may be a methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbonyl,s-butoxycarbonyl, t-butoxycarbonyl, pentoxycarbonyl, isopentoxycarbonyl,2-methylbutoxycarbonyl, neopentoxycarbonyl, 1-ethylpropoxycarbonyl,hexyloxycarbonyl, 4-methylpentoxycarbonyl, 3-methylpentoxycarbonyl,2-methylpentoxycarbonyl, 1-methylpentoxycarbonyl,3,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl,1,1-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl,1,3-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl or2-ethylbutoxycarbonyl group, preferably a carbonyl group to which a C₁to C₃ alkoxy group is bonded (a C₂ to C₄ alkoxycarbonyl group), morepreferably a methoxycarbonyl or ethoxycarbonyl group, still furtherpreferably a methoxycarbonyl group.

In the present invention, “the phenylthio group which may be substituted(The substituent is a substituent selected from the substituent GroupA.)” is a phenylthio group which may be substituted by the same ordifferent 1 to 5 substituent(s) selected from the group consisting ofthe above-mentioned “halogen atom”, the above-mentioned “C₁ to C₆ alkylgroup”, the above-mentioned “C₁ to C₆ haloalkyl group”, theabove-mentioned “C₃ to C₆ cycloalkyl group”, a cyano group and theabove-mentioned “tri(C₁ to C₆ alkyl)silyl group”, and for example, itmay beta phenylthio, fluorophenylthio, difluorophenylthio,trifluorophenylthio, chlorophenylthio, dichlorophenylthio,trichlorophenylthio, fluorochlorophenylthio, methylphenylthio,dimethylphenylthio, trimethylphenylthio, tetramethylphenylthio,pentamethylphenylthio, ethylphenylthio, fluoro(methyl)phenylthio,chloro(methyl)phenylthio, bromo(methyl)phenylthio,cyclopropylphenylthio, cyclopropyl(fluoro)phenylthio,chloro(cyclopropyl)phenylthio, cyclopropyl(methyl)phenylthio,(trifluoromethyl)phenylthio or fluoro(trifluoromethyl)phenylthio group,preferably a phenylthio group which may be substituted by the same ordifferent 1 to 3 substituent(s) selected from the group consisting of afluorine atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group,“a C₁ to C₃ alkyl group which is substituted by the same or different 1to 3 substituent(s) selected from the group consisting of a fluorineatom, a chlorine atom and a bromine atom”, a C₃ to C₄ cycloalkyl group,a cyano group and a tri(C₁ to C₃ alkyl)silyl group, more preferably aphenylthio, chlorophenylthio, methylphenylthio, trifluorophenylthio orcyanophenylthio group.

In the present invention, “the C₁ to C₆ alkylthio group” is a straightor branched alkylthio group having 1 to 6 carbon atoms, and for example,it may be a methylthio, ethylthio, propylthio, isopropylthio, butylthio,isobutylthio, s-butylthio, t-butylthio, pentylthio, isopentylthio,2-methylbutylthio, neopentylthio, 1-ethylpropylthio, hexylthio,4-methylpentylthio, 3-methylpentylthio, 2-methylpentylthio,1-methylpentylthio, 3,3-dimethylbutylthio, 2,2-dimethylbutylthio,1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio,2,3-dimethylbutylthio or 2-ethylbutylthio group, preferably a straightor branched alkylthio group having 1 to 3 carbon atoms (a C₁ to C₃alkylthio group), more preferably a methylthio or ethylthio group, stillfurther preferably a methylthio group.

In the present invention, “the C₁ to C₆ alkylsulfinyl group” is astraight or branched alkylsulfinyl group having 1 to 6 carbon atoms, andfor example, it may be a methylsulfinyl, ethylsulfinyl, propylsulfinyl,isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl,t-butylsulfinyl, pentylsulfinyl, isopentylsulfinyl,2-methylbutylsulfinyl, neopentylsulfinyl, 1-ethylpropylsulfinyl,hexylsulfinyl, 4-methylpentylsulfinyl, 3-methylpentylsulfinyl,2-methylpentylsulfinyl, 1-methylpentylsulfinyl,3,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl,1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl,1,3-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl or2-ethylbutylsulfinyl group, preferably a straight or branchedalkylsulfinyl group having 1 to 3 carbon atoms (a C₁ to C₃ alkylsulfinylgroup), more preferably a methylsulfinyl or ethylsulfinyl group, stillfurther preferably a methylsulfinyl group.

In the present invention, “the C₁ to C₆ alkylsulfonyl group” is astraight or branched alkylsulfonyl group having 1 to 6 carbon atoms, andfor example, it may be a methylsulfonyl, ethylsulfonyl, propylsulfonyl,isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl,t-butylsulfonyl, pentylsulfonyl, isopentylsulfonyl,2-methylbutylsulfonyl, neopentylsulfonyl, 1-ethylpropylsulfonyl,hexylsulfonyl, 4-methylpentylsulfonyl, 3-methylpentylsulfonyl,2-methylpentylsulfonyl, 1-methylpentylsulfonyl,3,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl,1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl,1,3-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl or2-ethylbutylsulfonyl group, preferably a straight or branchedalkylsulfonyl group having 1 to 3 carbon atoms (a C₁ to C₃ alkylsulfonylgroup), more preferably a methylsulfonyl or ethylsulfonyl group, stillfurther preferably a methylsulfonyl group.

In the present invention, “the C₁ to C₄ alkylenedioxy group” is astraight or branched alkylenedioxy group having 1 to 4 carbon atoms, andfor example, it may be a methylenedioxy, ethylenedioxy, propylenedioxy,trimethylenedioxy or tetramethylenedioxy group, preferably analkylenedioxy group having 1 to 2 carbon atoms, more preferably a1,2-ethylenedioxy group.

In the present invention, “the C₁ to C₆ alkoxyimino group” is a straightor branched alkoxyimino group having 1 to 6 carbon atoms, and forexample, it may be a methoxyimino, ethoxyimino, propoxyimino,isopropoxyimino, butoxyimino, isobutoxyimino, s-butoxyimino,t-butoxyimino, pentoxyimino, isopentoxyimino, 2-methylbutoxyimino,neopentoxyimino, 1-ethylpropoxyimino, hexyloxyimino,4-methylpentoxyimino, 3-methylpentoxyimino, 2-methylpentoxyimino,1-methylpentoxyimino, 3,3-dimethylbutoxyimino, 2,2-dimethylbutoxyimino,1,1-dimethylbutoxyimino, 1,2-dimethylbutoxyimino,1,3-dimethylbutoxyimino, 2,3-dimethylbutoxyimino or 2-ethylbutoxyiminogroup, preferably a straight or branched alkoxyimino group having 1 to 3carbon atoms (a C₁ to C₃ alkoxyimino group), more preferably amethoxyimino or ethoxyimino group, still further preferably amethoxyimino group.

In the present invention, “the C₁ to C₆ alkyl group which may besubstituted (The substituent is a substituent selected from thesubstituent Group B.)” is the above-mentioned “C₁ to C₆ alkyl group”which may be substituted by the above-mentioned “a halogen atom”, or bythe above-mentioned “C₃ to C₆ cycloalkyl group”, a cyano group, theabove-mentioned “C₂ to C₇ alkylcarbonyl group”, the above-mentioned “C₂to C₇ alkoxycarbonyl group”, a phenyl group, the above-mentioned “C₁ toC₆ alkoxy group”, the above-mentioned “C₁ to C₆ alkylthio group”, theabove-mentioned “C₁ to C₆ alkylsulfinyl group”, the above-mentioned “C₁to C₆ alkylsulfonyl group”, the above-mentioned “C₁ to C₄ alkylenedioxygroup”, a hydroxyimino group or the above-mentioned “C₁ to C₆alkoxyimino group”, and for example, it may be a fluoromethyl,difluoromethyl, trifluoromethyl, 2,2,2-trichloroethyl,cyclopropylmethyl, cyanomethyl, acetylmethyl, acetylethyl,methoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylmethyl,ethoxycarbonylethyl, benzyl, methoxmethyl, methoxyethyl, ethoxymethyl,ethoxyethyl, methylthiomethyl, methylthioethyl, ethylthiomethyl,ethylthioethyl, methylsulfinylmethyl, methylsulfonylmethyl,2-(1,3-dioxolanyl), hydroxyiminomethyl or methoxyiminomethyl group,preferably a C₁ to C₃ alkyl group substituted by the same or different 1to 3 substituent(s) selected from the group consisting of a fluorineatom, a chlorine atom and a bromine atom, or a C₁ to C₃ alkyl groupwhich may be substituted by a C₃ to C₄ cycloalkyl group, a cyano group,a C₂ to C₄ alkylcarbonyl group, a C₂ to C₄ alkoxycarbonyl group, aphenyl group, a C₁ to C₃ alkoxy group, a C₁ to C₃ alkylthio group, a C₁to C₃ alkylsulfinyl group, a C₁ to C₃ alkylsulfonyl group, a C₁ to C₂alkylenedioxy group, a hydroxyimino group or a C₁ to C₃ alkoxyiminogroup, more preferably a C₁ to C₂ alkyl group substituted by the same 1to 3 fluorine atom(s) or chlorine atom(s), or a C₁ to C₂ alkyl groupwhich may be substituted by a cyclopropyl group, a cyano group, a C₂ toC₃ alkylcarbonyl group, a C₂ to C₃ alkoxycarbonyl group, a phenyl group,a C₁ to C₂ alkoxy group, a C₁ to C₂ alkylthio group, a C₁ to C₂alkylsulfinyl group, a C₁ to C₂ alkylsulfonyl group, an ethylenedioxygroup, a hydroxyimino group or a C₁ to C₂ alkoxyimino group.

In the present invention, “the substituted C₂ to C₆ alkenyl group (Thesubstituent is a cyano group or a nitro group.) ” is the above-mentioned“C₂ to C₆ alkenyl group” substituted by a cyano group or a nitro group,preferably a C₂ to C₃ alkenyl group substituted by a cyano group or anitro group, more preferably a cyanovinyl or nitrovinyl group.

In the present invention, “the C₂ to C₆ alkynyl group” is a straight orbranched alkynyl group having 2 to 6 carbon atoms, and for example, itmay be ethynyl, 2-propynyl, 1-methyl-2-propynyl, 1-ethyl-2-propynyl,2-butynyl, 1-methyl-2-butynyl, 1-ethyl-2-butynyl, 3-butynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl-3-butynyl, 2-pentynyl,1-methyl-2-pentynyl, 1-ethyl-2-pentynyl, 3-pentynyl,1-methyl-3-pentynyl, 2-methyl-3-pentynyl, 4-pentynyl,1-methyl-4-pentynyl, 2-methyl-4-pentynyl, 2-hexynyl, 3-hexynyl,4-hexynyl or 5-hexynyl, preferably a straight or branched alkynyl grouphaving 3 to 4 carbon atoms (a C₃ to C₄ alkynyl group), more preferablyan ethynyl, 1-propynyl or 2-propynyl group.

In the present invention, “the amino group which may be substituted (Thesubstituent is a substituent selected from the substituent Group D.)” isan amino group which may be substituted by the same or different 1 to 2substituent(s) selected from the group consisting of the above-mentioned“C₁ to C₆ alkyl group”, the above-mentioned “C₂ to C₇ alkylcarbonylgroup”, the above-mentioned “C₂ to C₇ alkoxycarbonyl group”, theabove-mentioned “di(C₁ to C₆ alkyl)carbamoyl group” and theabove-mentioned “C₁ to C₆ alkylsulfonyl group”, and for example, it maybe an amino, methylamino, ethylamino, propylamino, isopropylamino,butylamino, isobutylamino, s-butylamino, t-butylamino, pentylamino,isopentylamino, (2-methylbutyl)amino, neopentylamino,(1-ethylpropyl)amino, hexylamino, (4-methylpentyl)amino,(3-methylpentyl)amino, (2-methylpentyl)amino, (1-methylpentyl)amino,(3,3-dimethylbutyl)amino, (2,2-dimethylbutyl)amino,(1,1-dimethylbutyl)amino, (1,2-dimethylbutyl)amino,(1,3-dimethylbutyl)amino, (2,3-dimethylbutyl)amino, (2-ethylbutyl)amino,dimethylamino, (methyl)(ethyl)amino, diethylamino, dipropylamino,(methyl)(isopropyl)amino, di(isopropyl)amino, dibutylamino,di(isobutyl)amino, di(s-butyl)amino, di(t-butyl)amino, dipentylamino,diisopentylamino, di(2-methylbutyl)amino, dineopentylamino,di(1-ethylpropyl)amino, dihexylamino, di(4-methylpentyl)amino,di(3-methylpentyl)amino, di(2-methylpentyl)amino,di(1-methylpentyl)amino, di(3,3-dimethylbutyl)amino,di(2,2-dimethylbutyl)amino, di(1,1-dimethylbutyl)amino,di(1,2-dimethylbutyl)amino, di(1,3-dimethylbutyl)amino,di(2,3-dimethylbutyl)amino, di(2-ethylbutyl)amino, acetylamino,propionylamino, butanoylamino, (2-methylpropanoyl)amino, pentanoylamino,(2,2-dimethylpropanoyl)amino, (2,2-dimethylpentanoyl)amino,(2-methylbutanoyl)amino, (3-methylbutanoyl)amino, hexanoylamino,heptanoyl amino, (3,3-dimethylbutanoyl)amino, methoxycarbonylamino,ethoxycarbonylamino, propoxycarbonylamino, isopropoxycarbonylamino,butoxycarbonylamino, isobutoxycarbonylamino, s-butoxycarbonylamino,t-butoxycarbonylamino, pentoxycarbonylamino, isopentoxycarbonylamino,(2-methylbutoxycarbonyl)amino, neopentoxycarbonylamino,(1-ethylpropoxycarbonyl)amino, hexyloxycarbonylamino,(4-methylpentoxycarbonyl)amino, (3-methylpentoxycarbonyl)amino,(2-methylpentoxycarbonyl)amino, (1-methylpentoxycarbonyl)amino,(3,3-dimethylbutoxycarbonyl)amino, (2,2-dimethylbutoxycarbonyl)amino,(1,1-dimethylbutoxycarbonyl)amino, (1,2-dimethylbutoxycarbonyl)amino,(1,3-dimethylbutoxycarbonyl)amino, (2,3-dimethylbutoxycarbonyl)amino,(2-ethylbutoxycarbonyl)amino, dimethylcarbamoylamino,(methylethylcarbamoyl)amino, diethylcarbamoylamino,dipropylcarbamoylamino, dibutylcarbamoylamino, dihexylcarbamoylamino,methylsulfonylamino, ethylsulfonylamino, propylsulfonylamino,isopropylsulfonylamino, butylsulfonylamino, t-butylsulfonylamino orhexylsulfonylamino, preferably an amino group which may be substitutedby the same or different 1 to 2 C₁ to C₃ alkyl groups, or a C₂ to C₄alkylcarbonyl group, a C₂ to C₄ alkoxycarbonyl group, a di(C₁ to C₃alkyl)carbamoyl group or a C₁ to C₃ alkylsulfonyl group, more preferablyan methylamino, ethylamino, dimethylamino, diethylamino, acetylamino,propionylamino, (2-methylpropanoyl)amino, (2,2-dimethylpropanoyl)amino,methoxycarbonylamino, ethoxycarbonylamino, dimethylcarbamoylamino,diethylcarbamoylamino, methylsulfonylamino or ethylsulfonylamino group.

In the present invention, “the C₁ to C₆ haloalkoxy group” is theabove-mentioned “C₁ to C₆ alkoxy group” substituted by the same ordifferent 1 to 5 above-mentioned “halogen atoms”, and for example, itmay be a chloromethoxy, dichloromethoxy, trichloromethoxy,1-chloroethoxy, 2-chloroethoxy, 2,2,2-trichloroethoxy, 1-chloropropoxy,3-chloropropoxy, 1-chlorobutoxy, 4-chlorobutoxy, fluoromethoxy,difluoromethoxy, trifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy,2,2,2-trifluoroethoxy, pentafluoroethoxy, fluorochloromethoxy,bromomethoxy, 1-bromoethoxy, 2-bromoethoxy or iodomethoxy group,preferably a C₁ to C₃ alkoxy group substituted by the same or different1 to 3 substituent(s) selected from the group consisting of a fluorineatom, a chlorine atom and a bromine atom, more preferably a C₁ to C₂alkoxy group substituted by the same 1 to 3 fluorine atom(s) or chlorineatom(s), still further preferably a fluoromethoxy, difluoromethoxy,trifluoromethoxy or 2,2,2-trichloroethoxy group, particularly preferablya trifluoromethoxy group.

In the present invention, “the substituted C₃ to C₆ cycloalkyl group(The substituent is a substituent selected from the substituent GroupC.)” is the above-mentioned “C₃ to C₆ cycloalkyl group” substituted bythe same or different 1 to 5 substituent(s) selected from the groupconsisting of the above-mentioned “halogen atom”, the above-mentioned“C₁ to C₆ alkyl group which may be substituted (The substituent is asubstituent selected from the substituent Group B.)”, theabove-mentioned “C₃ to C₆ cycloalkyl group”, the above-mentioned “C₂ toC₆ alkenyl group”, a cyano group, the above-mentioned “C₂ to C₇alkylcarbonyl group”, a benzoyl group, a carboxyl group, theabove-mentioned “C₂ to C₇ alkoxycarbonyl group”, a carbamoyl group, theabove-mentioned “di(C₁ to C₆ alkyl)carbamoyl group”, the above-mentioned“phenyl group which may be substituted (The substituent is a substituentselected from the substituent Group A.)”, the above-mentioned “5 or6-membered heterocyclic group (the heterocycle contains one nitrogenatom, oxygen atom or sulfur atom in the ring, and may contain further 1or 2 nitrogen atom(s).)”, the above-mentioned “amino group which may besubstituted (The substituent is a substituent selected from thesubstituent Group D.)”, a nitro group, a hydroxyl group, theabove-mentioned “C₁ to C₆ alkoxy group”, the above-mentioned “C₁ to C₆haloalkoxy group”, a phenoxy group, the above-mentioned “C₁ to C₆alkylthio group”, a phenylthio group, the above-mentioned “C₁ to C₆alkylsulfinyl group” and the above-mentioned “C₁ to C₆ alkylsulfonylgroup”, and for example, it may be a fluorocyclopropyl,difluorocyclopropyl, chlorocyclopropyl, dichlorocyclopropyl,bromocyclopropyl, dibromocyclopropyl, iodocyclopropyl,methylcyclopropyl, ethylcyclopropyl, propylcyclopropyl,isopropylcyclopropyl, butylcyclopropyl, t-butylcyclopropyl,hexylcyclopropyl, cyclopropylcyclopropyl, cyclobutylcyclopropyl,cyclopentylcyclopropyl, (fluoromethyl)cyclopropyl,(chloromethyl)cyclopropyl, (bromomethyl)cyclopropyl,(difluoromethyl)cyclopropyl, (trifluoromethyl)cyclopropyl,(trichloromethyl)cyclopropyl, (2,2,2-trifluoroethyl)cyclopropyl,(2,2,2-trichloroethyl)cyclopropyl, vinylcyclopropyl,(methoxymethyl)cyclopropyl, (ethoxymethyl)cyclopropyl,(isopropoxymethyl)cyclopropyl, (methylthiomethyl)cyclopropyl,(ethylthiomethyl)cyclopropyl, (isopropylthiomethyl)cyclopropyl,(methylsulfinylmethyl)cyclopropyl, (ethylsulfinylmethyl)cyclopropyl,(methylsulfonylmethyl)cyclopropyl, (ethylsulfonylmethyl)cyclopropyl,cyanocyclopropyl, (1-methoxyiminoethyl)cyclopropyl, acetylcyclopropyl,propionylcyclopropyl, benzoylcyclopropyl, carboxylcyclopropyl,methoxycarbonylcyclopropyl, ethoxycarbonylcyclopropyl,carbamoylcyclopropyl, (dimethylcarbamoyl)cyclopropyl,(diethylcarbamoyl)cyclopropyl, phenylcyclopropyl,(fluorophenyl)cyclopropyl, (chlorophenyl)cyclopropyl, tolylcyclopropyl,furylcyclo-7 propyl, thienylcyclopropyl, pyridylcyclopropyl,aminocyclopropyl, (methylamino)cyclopropyl, (dimethylamino)cyclopropyl,(acetylamino)cyclopropyl, (methoxycarbonylamino)cyclopropyl,(3,3-dimethylureido)cyclopropyl, (methylsulfonylamino)cyclopropyl,nitrocyclopropyl, hydroxycyclopropyl, methoxycyclopropyl,ethoxycyclopropyl, (trifluoromethoxy)cyclopropyl, phenoxycyclopropyl,methylthiocyclopropyl, ethylthiocyclopropyl, phenylthiocyclopropyl,methylsulfinylcyclopropyl, ethylsulfinylcyclopropyl,methylsulfonylcyclopropyl, ethylsulfonylcyclopropyl,dimethylcyclopropyl, methyl(ethyl)cyclopropyl, diethylcyclopropyl,biscyanocyclopropyl, trimethylcyclopropyl, tetramethylcyclopropyl,pentamethylcyclopropyl, methylcyclobutyl, vinylcyclobutyl,cyanocyclobutyl, carboxylcyclobutyl, acetylcyclobutyl,methoxycarbonylcyclobutyl or aminocyclobutyl group, preferably a C₃ toC₄ cycloalkyl group substituted by the same or different 1 to 5substituent(s) selected from the group consisting of a fluorine atom, achlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₃ to C₄cycloalkyl group and a cyano group, or substituted by “a C₁ to C₃ alkylgroup substituted by the same or different 1 to 3 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atomand a bromine atom, or a C₁ to C₃ alkyl group substituted by a C₃ to C₄cycloalkyl group, a cyano group, a C₂ to C₄ alkylcarbonyl group, a C₂ toC₄ alkoxycarbonyl group, a phenyl group, a C₁ to C₃ alkoxy group, a C₁to C₃ alkylthio group, a C₁ to C₃ alkylsulfinyl group, a C₁ to C₃alkylsulfonyl group, a C₁ to C₂ alkylenedioxy group, an imino group or aC₁ to C₃ alkoxyimino group”, a C₂ to C₄ alkenyl group, a C₂ to C₄alkylcarbonyl group, a benzoyl group, a carboxyl group, a C₂ to C₄alkoxycarbonyl group, a carbamoyl group, a di(C₁ to C₃ alkyl)carbamoylgroup, “a phenyl group which may be substituted by the same or different1 to 3 substituent(s) selected from the group consisting of a fluorineatom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, “a C₁ toC₃ alkyl group substituted by the same or different 1 to 3substituent(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom”, a C₃ to C₄ cycloalkyl group, a cyanogroup and a tri(C₁ to C₃ alkyl)silyl group”, a 5-membered heterocyclicgroup (the heterocycle contains one nitrogen atom, oxygen atom or sulfuratom in the ring.), “an amino group which may be substituted by the sameor different 1 to 2 C₁ to C₃ alkyl group, or by a C₂ to C₄ alkylcarbonylgroup, a C₂ to C₄ alkoxycarbonyl group, a di(C₁ to C₃ alkyl)carbamoylgroup or a C₁ to C₃ alkylsulfonyl group”, a nitro group, a hydroxylgroup, a C₁ to C₃ alkoxy group, a C₁ to C₃ haloalkoxy group, a phenoxygroup, a C₁ to C₃ alkylthio group, a phenylthio group, a C₁ to C₃alkylsulfinyl group or a C₁ to C₃ alkylsulfonyl group, more preferably acyclopropyl group substituted by the same or different 1 to 3substituent(s) selected from the group consisting of a chlorine atom, abromine atom, a C₁ to C₂ alkyl group, cyclopropyl group and a cyanogroup, or by “a C₁ to C₂ alkyl group substituted by a C₁ to C₂ alkylgroup which is substituted by the same 1 to 3 substituent(s) selectedfrom the group consisting of a chlorine atom and a bromine atom, orsubstituted by a cyclopropyl group, a cyano group, a C₂ to C₃alkylcarbonyl group, a C₂ to C₃ alkoxycarbonyl group, a phenyl group, aC₁ to C₂ alkoxy group, a C₁ to C₂ alkylthio group, a C₁ to C₂alkylsulfinyl group, a C₁ to C₂ alkylsulfonyl group, a 1,2-ethylenedioxygroup, an imino group or a C₁ to C₂ alkoxyimino group”, a C₂ to C₃alkenyl group, a C₂ to C₃ alkylcarbonyl group, a benzoyl group, acarboxyl group, a C₂ to C₃ alkoxycarbonyl group, a carbamoyl group, adi(C₁ to C₂ alkyl)carbamoyl group, “a phenyl group which may besubstituted by the same or different 1 to 2 substituent(s) selected fromthe group consisting of a chlorine atom, a bromine atom, a C₁ to C₂alkyl group, “a C₁ to C₂ alkyl group substituted by the same 1 to 3fluorine atom(s) or chlorine atom(s)”, a cyclopropyl group, a cyanogroup and a tri(C₁ to C₂ alkyl)-silyl group”, a furyl group, a thienylgroup, “an amino group which may be substituted by the same 1 to 2 C₁ toC₂ alkyl group(s), or by a C₂ to C₃ alkylcarbonyl group, a C₂ to C₃alkoxycarbonyl group, a di(C₁ to C₂ alkyl)carbamoyl group or a C₁ to C₂alkylsulfonyl group”, a nitro group, a hydroxyl group, a C₁ to C₂ alkoxygroup, a C₁ to C₂ haloalkoxy group, a phenoxy group, a C₁ to C₂alkylthio group, a phenylthio group, a C₁ to C₂ alkylsulfinyl group or aC₁ to C₂ alkylsulfonyl group.

In the present invention, “the C₄ to C₁₀ bicycloalkyl group” is abicyclic hydrocarbon having 4 to 10 carbon atoms, and for example, itmay be a bicyclobutyl, bicyclepentyl, bicyclohexyl, bicycloheptyl,bicyclooctyl, bicyclononyl or bicyclodecyl group, preferably abicyclehexyl or bicycleheptyl group, more preferably abicycle[3.1.0]hexyl or bicyclo[4.1.0]heptyl group, still furtherpreferably a bicyclo[3.1.0]hexan-6-yl group.

In the present invention, “the phenylsulfonyl group which may besubstituted (The substituent is a substituent selected from thesubstituent Group A.)” is a phenylsulfonyl group which may besubstituted by the same or different 1 to 5 substituent(s) selected fromthe group consisting of the above-mentioned “halogen atom”, theabove-mentioned “C₁ to C₆ alkyl group”, the above-mentioned “C₁ to C₆haloalkyl group”, the above-mentioned “C₃ to C₆ cycloalkyl group”, acyano group and the above-mentioned “tri(C₁ to C₆ alkyl)silyl group”,and for example, it may be a phenylsulfonyl, fluorophenylsulfonyl,difluorophenylsulfonyl, trifluorophenylsulfonyl, chlorophenylsulfonyl,dichlorophenylsulfonyl, trichlorophenylsulfonyl,fluorochlorophenylsulfonyl, methylphenylsulfonyl,dimethylphenylsulfonyl, trimethylphenylsulfonyl,tetramethylphenylsulfonyl, pentamethylphenylsulfonyl,ethylphenylsulfonyl, fluoro(methyl)phenylsulfonyl,chloro(methyl)phenylsulfonyl, bromo(methyl)phenylsulfonyl,cyclopropylphenylsulfonyl, cyclopropyl(fluoro)phenylsulfonyl,chloro(cyclopropyl)phenylsulfonyl, cyclopropyl(methyl)phenylsulfonyl,(trifluoromethyl)phenylsulfonyl or fluoro(trifluoromethyl)phenylsulfonylgroup, preferably a phenylsulfonyl group which may be substituted by thesame or different 1 to 3 substituent(s) selected from the groupconsisting of a fluorine atom, a chlorine atom, a bromine atom, a C₁ toC₃ alkyl group, “a C₁ to C₃ alkyl group substituted by the same ordifferent 1 to 3 substituent(s) selected from the group consisting of afluorine atom, a chlorine atom and a bromine atom”, a C₃ to C₄cycloalkyl group, a cyano group and a tri(C₁ to C₃ alkyl)silyl group,more preferably a phenylsulfonyl, chlorophenylsulfonyl,methylphenylsulfonyl, trifluorophenylsulfonyl or cyanophenylsulfonylgroup.

In the present invention, “the di(C₁ to C₆ alkyl)sulfamoyl group” is asulfamoyl group in which the same or different 2 above-mentioned “C₁ toC₆ alkyl groups” are bonded to the nitrogen atom, and for example, itmay be a dimethylsulfamoyl, methylethylsulfamoyl, diethylsulfamoyl,dipropylsulfamoyl, dibutylsulfamoyl or dihexylsulfamoyl, preferably asulfamoyl group to which the same or different 2 C₁ to C₃ alkyl groupsare bonded, more preferably a dimethylsulfamoyl or diethylsulfamoylgroup, still further preferably a dimethylsulfamoyl group.

In the present invention, “the 3- to 6-membered heterocyclic group whichmay be substituted (the heterocycle contains one nitrogen atom, oxygenatom or sulfur atom in the ring, and may contain further 1 or 2 nitrogenatom(s), or may be fused with a benzene ring. The substituent is asubstituent selected from the substituent Group E.)” is “a 3- to6-membered heterocyclic group which contains one nitrogen atom, oxygenatom or sulfur atom as a hetero atom, and may contain further 1 to 2nitrogen atom(s)” which may be substituted by the same or different 1 to3 substituent(s) selected from the group consisting of theabove-mentioned “halogen atom”, the above-mentioned “C₁ to C₆ alkylgroup” and the above-mentioned “C₁ to C₆ haloalkyl group”, or by ahydroxyl group, the above-mentioned “phenylsulfonyl group which may besubstituted (The substituent is a substituent selected from thesubstituent Group A.)” or the above-mentioned “di(C₁ to C₆alkyl)sulfamoyl group”, or may be fused with a benzene ring, preferably“a 3- to 6-membered heterocyclic group which contains one nitrogen atom,oxygen atom or sulfur atom as a hetero atom, and may contain further onenitrogen atom” which may be substituted by the same or different 1 to 2substituent(s) selected from the group consisting of a fluorine atom, achlorine atom, a bromine atom, a C₁ to C₃ alkyl group and “a C₁ to C₃alkyl group substituted by the same or different 1 to 3 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atomand a bromine atom”, or may be substituted by a hydroxyl group, “aphenylsulfonyl group which may be substituted by the same or different 1to 3 substituent(s) selected from the group consisting of a fluorineatom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, “a C₁ toC₃ alkyl group substituted by the same or different 1 to 3substituent(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom”, a C₃ to C₄ cycloalkyl group, a cyanogroup and a tri(C₁ to C₃ alkyl)silyl group” or “a sulfamoyl group towhich the same or different 2 C₁ to C₃ alkyl groups are bonded”, or maybe fused with a benzene ring, more preferably an aziridine, oxiranyl,oxetanyl, pyrrolyl, furyl, thienyl, pyrazolyl, thiazolyl, pyridyl,benzimidazolyl or benzothiazolyl, each of which may be substituted bythe same 1 to 2 substituent(s) selected from the group consisting of achlorine atom, a bromine atom, methyl group, ethyl group andtrifluoromethyl group, or may be substituted by a hydroxyl group,phenylsulfonyl group, tolylsulfonyl group or dimethylsulfamoyl group,still further preferably a thienyl, pyrazolyl, thiazolyl group which maybe substituted by the same or different 1 to 2 substituent(s) selectedfrom the group consisting of a chlorine atom, methyl group andtrifluoromethyl group.

In the present invention, “the (C₁ to C₆ alkoxy)C₁ to C₆ alkoxy group”is an alkoxy group having 1 to 6 carbon atoms to which an alkoxy grouphaving 1 to 6 carbon atoms is bonded, and for example, it may be amethoxymethoxy, ethoxymethoxy, propoxymethoxy, butoxymethoxy,s-butoxymethoxy, t-butoxymethoxy, pentyloxymethoxy, hexyloxymethoxy,methoxyethoxy, ethoxyethoxy, propoxyethoxy, butoxyethoxy,methoxypropoxy, methoxybutoxy, methoxypentyloxy or methoxyhexyloxygroup, preferably an alkoxy group having 1 to 3 carbon atoms to which analkoxy group having 1 to 3 carbon atoms is substituted, more preferablya methoxyethoxy, ethoxyethoxy or ethoxymethoxy group.

In the present invention, “a phenoxy group which may be substituted (Thesubstituent is a hydroxyl group or a pyridazinyloxy group substituted bya substituent(s) selected from the group consisting of a halogen atomand a C₁ to C₆ alkoxy group.)” is a phenoxy group which may besubstituted by one hydroxyl group, or a phenoxy group substituted by apyridazinyloxy group which is substituted by the same or different 1 to3 substituent(s) selected from the group consisting of theabove-mentioned “halogen atom” and the above-mentioned “C₁ to C₆ alkoxygroup”, preferably a hydroxyphenoxy group, or a phenoxy groupsubstituted by a pyridazinyloxy group which is substituted by the sameor different 1 to 2 substituent(s) selected from the group consisting ofa fluorine atom, a chlorine atom, a bromine atom and C₁ to C₃ alkoxygroup, more preferably a phenoxy group substituted by a pyridazinyloxygroup which is substituted by each one of a chlorine atom, and a methoxyor ethoxy group.

In the present invention, “the 5- to 6-membered heterocycloxy groupwhich may be substituted (the heterocycle contains one nitrogen atom,oxygen atom or sulfur atom in the ring, and may contain further 1 or 2nitrogen atom(s). The substituent is a substituent selected from thesubstituent Group E.)” is “a 5- to 6-membered heterocycloxy group whichcontains one nitrogen atom, oxygen atom or sulfur atom as a heteroatom,and may contain further 1 to 2 nitrogen atom(s)” which may besubstituted by the same or different 1 to 2 substituent(s) selected fromthe group consisting of the above-mentioned “halogen atom”, theabove-mentioned “C₁ to C₆ alkyl group”, the above-mentioned “C₁ to C₆haloalkyl group”, a hydroxyl group, the above-mentioned “phenylsulfonylgroup which may be substituted (The substituent is a substituentselected from the substituent Group A.)” and the above-mentioned “di(C₁to C₆ alkyl)sulfamoyl group”, preferably “a 5- to 6-memberedheterocycloxy group which contains one nitrogen atom, oxygen atom orsulfur atom as a heteroatom, and may contain further one nitrogen atom”which may be substituted by the same or different 1 to 2 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atom,a bromine atom, a C₁ to C₃ alkyl group, “a C₁ to C₃ alkyl groupsubstituted by the same or different 1 to 3 substituent(s) selected fromthe group consisting of a fluorine atom, a chlorine atom and a bromineatom”, a hydroxyl group, “a phenylsulfonyl group which may besubstituted by the same or different 1 to 3 substituent(s) selected fromthe group consisting of a fluorine atom, a chlorine atom, a bromineatom, a C₁ to C₃ alkyl group, “a C₁ to C₃ alkyl group substituted by thesame or different 1 to 3 substituent(s) selected from the groupconsisting of a fluorine atom, a chlorine atom and a bromine atom”, a C₃to C₄ cycloalkyl group, a cyano group and a tri(C₁ to C₃ alkyl)silylgroup” and “a sulfamoyl group to which the same or different two C₁ toC₃ alkyl groups are bonded”, more preferably a pyridyloxy, pyrrolyloxy,furyloxy, thienyloxy, pyrazolyloxy, thiazolyloxy, pyrimidyloxy,pyrazinyloxy or a pyridazinyloxy group, each of which may be substitutedby 1 to 2 different substituents selected from the group consisting of achlorine atom, a bromine atom, a methyl group, an ethyl group, atrifluoromethyl group, a hydroxyl group, a phenylsulfonyl group, atolylsulfonyl group and a dimethylsulfamoyl group, still furtherpreferably a pyridazinyloxy group which may be substituted by a chlorineatom and a hydroxyl group.

In the present invention, “the phenylsulfonyloxy group which may besubstituted (The substituent is a substituent selected from thesubstituent Group A.)” is a phenylsulfonyloxy group which may besubstituted by the same or different 1 to 5 substituent(s) selected fromthe group consisting of the above-mentioned “halogen atom”, theabove-mentioned “C₁ to C₆ alkyl group”, the above-mentioned “C₁ to C₆haloalkyl group”, the above-mentioned “C₃ to C₆ cycloalkyl group”, acyano group and the above-mentioned “tri(C₁ to C₆ alkyl)silyl group”,and for example, it may be a phenylsulfonyloxy, fluorophenylsulfonyloxy,difluorophenylsulfonyloxy, trifluorophenylsulfonyloxy,chlorophenylsulfonyloxy, dichlorophenylsulfonyloxy,trichlorophenylsulfonyloxy, fluorochlorophenylsulfonyloxy,methylphenylsulfonyloxy, dimethylphenylsulfonyloxy,trimethylphenylsulfonyloxy, tetramethylphenylsulfonyloxy,pentamethylphenylsulfonyloxy, ethylphenylsulfonyloxy,fluoro(methyl)phenylsulfonyloxy, chloro(methyl)phenylsulfonyloxy,bromo(methyl)phenylsulfonyloxy, cyclopropylphenylsulfonyloxy,cyclopropyl(fluoro)phenylsulfonyloxy,chloro(cyclopropyl)phenylsulfonyloxy,cyclopropyl(methyl)phenylsulfonyloxy, (trifluoromethyl)phenylsulfonyloxyor fluoro(trifluoromethyl)phenylsulfonyloxy group, preferably aphenylsulfonyloxy group which may be substituted by the same ordifferent 1 to 3 substituent(s) selected from the group consisting of afluorine atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group,“a C₁ to C₃ alkyl group substituted by the same or different 1 to 3substituent(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom”, a C₃ to C₄ cycloalkyl group, a cyanogroup and a tri(C₁ to C₃ alkyl)silyl group, more preferably aphenylsulfonyloxy, chlorophenylsulfonyloxy, methylphenylsulfonyloxy,trifluorophenylsulfonyloxy or cyanophenylsulfonyloxy group.

In R³, R⁴, R⁵, R⁶ and R⁷ according to the present invention, “the 3- to6-membered cyclic hydrocarbon group which may be substituted, which isformed by the adjacent two of them with carbon atoms to which therespective substituents are bonded (the cyclic hydrocarbon may beinterrupted by 1 to 2 hetero atom(s) selected from the group consistingof a nitrogen atom, an oxygen atom and a sulfur atom. The substituent isa halogen atom, a C₁ to C₆ alkyl group, a hydroxy-C₁ to C₆ alkyl group,a C₁ to C₆ alkoxy group, an oxo group, a hydroxyimino group or a C₁ toC₆ alkoxyimino group, and when the C₁ to C₆ alkyl group is substituted,it may form another 3-membered ring by binding with the other C₁ to C₆alkyl group or a carbon atom(s)in the cyclic hydrocarbon.)” is asaturated or unsaturated 3- to 6-membered cyclic hydrocarbon group whichmay be substituted by the same or different 1 to 4 substituent(s)selected from the group consisting of the above-mentioned “halogenatom”, the above-mentioned “C₁ to C₆ alkyl group”, the above-mentioned“C₁ to C₆ alkyl group” substituted by 1 to 2 hydroxyl group(s), theabove-mentioned “C₁ to C₆ alkoxy group”, an oxo group, a hydroxyiminogroup and the above-mentioned “C₁ to C₆ alkoxyimino group”, and may beinterrupted by the same or different 1 to 2 hetero atom(s) selected fromthe group consisting of a nitrogen atom, an oxygen atom and a sulfuratom, and further may form a cyclopropane ring on the cyclic hydrocarbongroup, preferably a group represented by —CH₂—, —CH₂CH₂—, —CH₂CH₂CH₂—,—CH (CH₃) CH₂CH₂—, —CH₂CH (CH₃) CH₂—, —C(CH₃)₂CH₂CH₂—, —CH₂C(CH₃) ₂CH₂—,—CH (OCH₃) CH₂CH₂—, —C(OCH₃)₂CH₂CH₂—, —CH₂C (OCH₃)₂CH₂—, —C(═O) CH₂CH₂—,—CH₂C(═O) CH₂—, —C(═NOCH₃) CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH (CH₃)CH₂CH₂CH₂—, —C(CH₃)₂CH₂CH₂CH₂—, —CH (OCH₃) CH₂CH₂CH₂—, —CH═CH—CH═CH—,—OCH₂CH₂—, —OCH (CH₃) CH₂—, —OCH₂CH(CH₃)—, —OC(CH₃)₂CH₂—, —OCH═CH—,—OC(CH₃)═CH—, —OCH═C(CH₃)—, —SCH═CH—, —N═CH—CH═CH—, —OCH₂O—, —OCH(CH₃)O—, —OC(CH₃)₂O—, —OCF₂O—, —OCH₂CH₂O—, —OCH═N—, —OC(CH₃) ═N—,

more preferably a group represented by —CH₂CH₂—, —CH₂CH₂CH₂——CH (CH₃)CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —OCH₂CH₂—, —OCH═CH—,—OCH═C(CH₃)—, —SCH═CH—, —N═CH—CH═CH—, —OCH₂O—, —OCH₂CH₂O—,

still further preferably a group represented by —CR₂CR₂CR₂—, —CH (CH₃)CH₂CH₂—, —OCH₂CH₂—, —OCH═CH— or

The compound (I) of the present invention can be made a salt to begenerally used in agricultural chemicals, and for example, it can bemade an alkali metal salt, an alkaline earth metal salt or an ammoniumsalt, and when a basic portion exists in the molecule, it can be made asalt, for example, a sulfate, hydrochloride, nitrate, phosphate, or thelike. These salts are included in the present invention so long as theycan be used as a herbicide for agricultural and horticultural chemicals.

In the present invention, “the alkali metal salt” may be, for example, asodium salt, potassium salt or lithium salt, preferably a sodium salt orpotassium salt.

In the present invention, “the alkaline earth metal salt” may be, forexample, a calcium salt or magnesium salt, preferably a calcium salt.

A solvate of the compounds of the present invention is also included inthe present invention.

In the compounds of the present invention, there are compounds having anasymmetric carbon(s), and in that case, the present invention alsoincludes a kind of optical isomers and a mixture of several kinds ofoptical isomers with an optional ratio.

In the present invention, “ester derivative” is a compound in which anacyl group bonds to an oxygen atom of a hydroxyl group bonded at the4-position of the pyridazine ring, and for example, a compound to whichis/are bonded a C₂ to. C₁₅ alkylcarbonyl group which may be substituted[The substituent is the same or different 1 to 3 substituent(s) selectedfrom the group consisting of a halogen atom, a C₁ to C₆ alkoxy group, aC₂ to C₇ alkoxycarbonyl group, a C₂ to C₆ alkenyloxycarbonyl group whichmay be substituted {The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a C₃ to C₆cycloalkyl group, a cyano group and a benzoyl group which may besubstituted (The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a halogen atom, aC₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂ to C₇alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a C₃ to C₆ cycloalkenyloxycarbonyl group which may besubstituted {The substituent is the same or different 1 to 2substituent(s) selected from the group consisting of an oxo group and abenzoyl group which may be substituted (The substituent is the same ordifferent 1 to 3 substituent(s) selected from the group consisting of ahalogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂to C₇ alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a 5 or 6-membered heterocycloxycarbonyl group which may besubstituted {the heterocycle contains one nitrogen atom, oxygen atom orsulfur atom in the ring, and may contain further 1 or 2 nitrogenatom(s). The substituent is the same or different 1 to 3 substituent(s)selected from the group consisting of a halogen atom, a C₁ to C₆ alkylgroup, a phenoxy group which may be substituted (The substituent is thesame or deferent 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃haloalkyl group, a C₃ to C₆ cycloalkyl group and a C₂ to C₇alkoxycarbonyl group.), a 2,3-dihydro-1H-indenyloxy group and a benzoylgroup which may be substituted (The substituent is the same or different1 to 3 substituent(s) selected from the group consisting of a halogenatom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂ to C₇alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a phenyl group which may be substituted (The substituent isthe same or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃haloalkyl group and a C₂ to C₇ alkoxycarbonyl group.), a phenoxy groupand a C₁ to C₆ alkylthio group.], a C₄ to C₇ cycloalkylcarbonyl group,an adamantylcarbonyl group, a C₃ to C₇ alkenylcarbonyl group which maybe substituted (The substituent is the same or different 1 to 2substituent(s) selected from the group consisting of a halogen atom anda phenyl group.), a C₃ to C₇ alkynylcarbonyl group, a benzoyl groupwhich may be substituted (The substituent is the same or different 1 to3 substituent(s) selected from the group consisting of a halogen atom, aC₁ to C₆ alkyl group which may be substituted (The substituent is thesame or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom and a phenyl group.), a cyano group, a C₂to C₇ alkylcarbonyl group, a C₂ to C₇ alkoxycarbonyl group, a C₃ to C₇alkenyloxycarbonyl group which may be substituted {The substituent isthe same or different 1 to 3 substituent(s) selected from the groupconsisting of a C₃ to C₆ cycloalkyl group, a cyano group and a benzoylgroup which may be substituted (The substituent is the same or different1 to 3 substituent(s) selected from the group consisting of a halogenatom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂ to C₇alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a C₄ to C₇ cycloalkenyloxycarbonyl group which may besubstituted {The substituent is the same or different 1 to 2substituent(s) selected from the group consisting of an oxo group and abenzoyl group which may be substituted (The substituent is the same ordifferent 1 to 3 substituent(s) selected from the group consisting of ahalogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂to C₇ alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a phenyl group, a nitro group, a C₁ to C₆ alkoxy group whichmay be substituted (The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a halogen atom anda phenyl group.), a phenoxy group, a 5 or 6-membered heterocyclicoxycarbonyl group which may be substituted {the heterocycle contains onenitrogen atom, oxygen atom or sulfur atom in the ring, and may containfurther 1 or 2 nitrogen atom(s). The substituent is the same ordifferent 1 to 3 substituent(s) selected from the group consisting of ahalogen atom, a C₁ to C₆ alkyl group, a phenoxy group which may besubstituted (The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a halogen atom, aC₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₃ to C₆ cycloalkylgroup and a C₂ to C₇ alkoxycarbonyl group.), a 2,3-dihydro-1H-indenyloxygroup and a benzoyl group which may be substituted (The substituent isthe same or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃haloalkyl group, a C₂ to C₇ alkoxycarbonyl group, a nitro group and a C₁to C₃ alkylsulfonyl group.).} and a 5 or 6-memberedheterocycloxysulfonyl group which may be substituted {the heterocyclecontains one nitrogen atom, oxygen atom or sulfur atom in the ring, andmay contain further 1 or 2 nitrogen atom(s). The substituent is the sameor different 1 to 3 substituent(s) selected from the group consisting ofa halogen atom, a C₁ to C₆ alkyl group, a phenoxy group which may besubstituted (The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a halogen atom, aC₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₃ to C₆ cycloalkylgroup and a C₂ to C₇ alkoxycarbonyl group.), a 2,3-dihydro-1H-indenyloxygroup and a benzoyl group which may be substituted (The substituent isthe same or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃haloalkyl group, a C₂ to C₇ alkoxycarbonyl group, a nitro group and a C₁to C₃ alkylsulfonyl group.).}.], a naphthoyl group, a 3- to 6-memberedheterocyclic carbonyl group which may be substituted {the heterocyclecontains one nitrogen atom, oxygen atom or sulfur atom in the ring, andmay contain further 1 or 2 nitrogen atom(s), or may form a 5- to6-membered spiro ring containing 1 to 2 oxygen atom(s) on an optionalcarbon atom in the heterocycle. The substituent is the same or different1 to 3 substituent(s) selected from the group consisting of a halogenatom, a C₁ to C₆ alkyl group which may be substituted (The substituentis the same or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom and a phenyl group.), a C₂ to C₇alkylcarbonyl group, a C₂ to C₇ alkoxycarbonyl group, a phenyl groupwhich may be substituted (The substituent is the same or different 1 to3 halogen atom(s).), a nitro group, a hydroxyl group, a C₁ to C₆ alkoxygroup, a phenoxy group, a C₁ to C₆ alkylthio group, a C₂ to C₆alkenylthio group and a phenylthio group.}, a 7 to 14-membered fused bi-or tri-cyclic heterocyclic carbonyl group which may be substituted (Theheterocycle contains one nitrogen atom, oxygen atom or sulfur atom inthe ring, and may contain further 1 to 2 nitrogen atom(s) or oxygenatom(s). The substituent is the same or different 1 to 3 substituent(s)selected from the group consisting of a halogen atom and a C₁ to C₆alkyl group.), a 5 or 6-membered heterocycle carbonylcarbonyl group (Theheterocycle contains one nitrogen atom, oxygen atom or sulfur atom inthe ring, and may contain further 1 or 2 nitrogen atom(s).), a C₂ to C₇alkoxycarbonyl group which may be substituted (The substituent is thesame or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom, a C₁ to C₆ alkoxy group and a phenylgroup.), a C₃ to C₇ alkenyloxycarbonyl group, a phenoxycarbonyl groupwhich may be substituted (The substituent is the same or different 1 to3 substituent(s) selected from the group consisting of a halogen atom, aC₁ to C₆ alkyl group, a cyano group, a C₂ to C₇ alkylcarbonyl group, aC₂ to C₇ alkoxycarbonyl group, a nitro group and a C₁ to C₆ alkoxygroup.), a fused polycyclic hydrocarbyloxycarbonyl group, a 5 or6-membered heterocycloxycarbonyl group which may be substituted {Theheterocycle contains one nitrogen atom, oxygen atom or sulfur atom inthe ring, and may contain further 1 or 2 nitrogen atom(s). Thesubstituent is the same or different 1 to 3 substituent(s) selected fromthe group consisting of a halogen atom, a C₁ to C₆ alkyl group, aphenoxy group which may be substituted (The substituent is the same ordifferent 1 to 3 substituent(s) selected from the group consisting of ahalogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₃to C₆ cycloalkyl group and a C₂ to C₇ alkoxycarbonyl group.), a2,3-dihydro-1H-indenyloxy group and a benzoyl group which may besubstituted (The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a halogen atom, aC₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂ to C₇alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a carbamoyl group which may be substituted {The substituentis the same or different 1 to 3 substituent(s) selected from the groupconsisting of a C₁ to C₆ alkyl group which may be substituted (Thesubstituent is the same or different 1 to 3 substituent(s) selected fromthe group consisting of a halogen atom, a C₂ to C₇ alkoxycarbonyl group,a cyano group, a phenyl group and a C₁ to C₆ alkoxy group.), a C₃ to C₆alkenyl group, a phenyl group, a C₂ to C₇ alkylcarbonyl group, a C₂ toC₇ alkoxycarbonyl group and a C₁ to C₆ alkoxy group.}, a (C₁ to C₆alkylthio)carbonyl group, a (phenylthio)carbonyl group, a C₁ to C₈alkylsulfonyl group which may be substituted (The substituent is thesame or different 1 to 3 halogen atom(s).), a phenylsulfonyl group whichmay be substituted [The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a halogen atom, aC₁ to C₆ alkyl group, a cyano group, a C₂ to C₇ alkylcarbonyl group, aC₂ to C₇ alkoxycarbonyl group, a nitro group, a C₁ to C₆ alkoxy group, aC₂ to C₆ alkenyloxysulfonyl group which may be substituted {Thesubstituent is the same or different 1 to 3 substituent(s) selected fromthe group consisting of a C₃ to C₆ cycloalkyl group, a cyano group and abenzoyl group which may be substituted (The substituent is the same ordifferent 1 to 3 substituent(s) selected from the group consisting of ahalogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂to C₇ alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a C₃ to C₆ cycloalkenyloxysulfonyl group which may besubstituted {The substituent is the same or different 1 to 2substituent(s) selected from the group consisting of an oxo group and abenzoyl group which may be substituted (The substituent is the same ordifferent 1 to 3 substituent(s) selected from the group consisting of ahalogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂to C₇ alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).} and a 5 or 6-membered heterocycloxysulfonyl group which may besubstituted {The heterocycle contains one nitrogen atom, oxygen atom orsulfur atom in the ring, and may contain further 1 or 2 nitrogenatom(s). The substituent is the same or different 1 to 3 substituent(s)selected from the group consisting of a halogen atom, a C₁ to C₆ alkylgroup, a phenoxy group which may be substituted (The substituent is thesame or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃haloalkyl group, a C₃ to C₆ cycloalkyl group and a C₂ to C₇alkoxycarbonyl group.), a 2,3-dihydro-1H-indenyloxy group and a benzoylgroup which may be substituted (The substituent is the same or different1 to 3 substituent(s) selected from the group consisting of a halogenatom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂ to C₇alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}.], a 5 or 6-membered heterocycloxysulfonyl group which may besubstituted {The heterocycle contains one nitrogen atom, oxygen atom orsulfur atom in the ring, and may contain further 1 or 2 nitrogenatom(s). The substituent is the same or different 1 to 3 substituent(s)selected from the group consisting of a halogen atom, a C₁ to C₆ alkylgroup, a phenoxy group which may be substituted (The substituent is thesame or different 1 to 3 substituent(s) selected from the groupconsisting of a halogen atom, a C₁ to C₆ alkyl group, a C₁ to C₃haloalkyl group, a C₃ to C₆ cycloalkyl group and a C₂ to C₇alkoxycarbonyl group.), a 2,3-dihydro-1H-indenyloxy group and a benzoylgroup which may be substituted (The substituent is the same or different1 to 3 substituent(s) selected from the group consisting of a halogenatom, a C₁ to C₆ alkyl group, a C₁ to C₃ haloalkyl group, a C₂ to C₇alkoxycarbonyl group, a nitro group and a C₁ to C₃ alkylsulfonylgroup.).}, a di(C₁ to C₆ alkyl)sulfamoyl group, a C₁ to C₆alkoxysulfonyl group, a di(C₁ to C₆ alkyl)phosphoryl group, a tri(C₁ toC₆ alkyl)silyl group or a triphenylsilyl group, preferably a compound towhich bonded is/arena C₂ to C₁₀ alkylcarbonyl group, a benzoyl groupwhich may be substituted (The substituent is the same or different 1 to2 substituent(s) selected from the group consisting of a fluorine atom,a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁ to C₃alkoxy group or a4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxycarbonyl group.),a pyrrolidinylcarbonyl group, azetidinylcarbonyl group, morpholinylcarbonyl group, a C₂ to C₅ alkoxycarbonyl group which may be substituted(The substituent is the same or different 1 to 3 substituent(s) selectedfrom the group consisting of a fluorine atom, a chlorine atom and abromine atom.), a di(C₁ to C₃ alkyl)carbamoyl group, a (C₁ to C₃ alkyl)(C₁ to C₃ alkoxy)carbamoyl group, a C₁ to C₃ alkylsulfonyl group whichmay be substituted (The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom.) or a phenylsulfonyl group which maybe substituted (The substituent is the same or different 1 to 2substituent(s) selected from the group consisting of a fluorine atom, achlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxysulfonyl groupand a nitro group.), more preferably a compound to which bonded is/are aC₂ to C₄ alkylcarbonyl group, a benzoyl group which may be substituted(The substituent is a methyl group or a4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxycarbonyl group.),a 1-acetidinylcarbonyl group, a 4-morpholinylcarbonyl group, a C₂ to C₃alkoxycarbonyl group which may be substituted (The substituent is 1 to 3chlorine atom(s).), a dimethylcarbamoyl group, amethoxy(methyl)carbamoyl group, a C₁ to C₃ alkylsulfonyl group which maybe substituted (The substituent is 1 to 3 fluorine atom(s).) or aphenylsulfonyl group which may be substituted (The substituent is achlorine atom, a methyl group, a4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxysulfonyl group ora nitro group.).

(a) In the present invention, R¹ is preferably a hydrogen atom, afluorine atom, a chlorine atom, a bromine atom, C₁ to C₃ alkyl group, C₁to C₃ haloalkyl group (The halogen atom is 1 to 3 fluorine atom(s).),cyclopropyl group, C₂ to C₃ alkenyl group, a cyano group, C₂ to C₄alkylcarbonyl group, di(C₁ to C₃ alkyl)carbamoyl group, a phenyl groupwhich may be substituted {The substituent is the same or different 1 to2 substituent(s) selected from the group consisting of a fluorine atom,a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁ to C₃haloalkyl group (The halogen atom is the same or different 1 to 3halogen atom(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom.), a cyclopropyl group, a cyano groupand a tri(C₁ to C₃ alkyl)silyl group.}, a furyl group, a thienyl group,a C₁ to C₃ alkoxy group, a phenoxy group which may be substituted {Thesubstituent is the same or different 1 to 2 substituent(s) selected fromthe group consisting of a fluorine atom, a chlorine atom, a bromineatom, a C₁ to C₃ alkyl group, a C₁ to C₃ haloalkyl group (The halogenatom is 1 to 3 fluorine atom(s).), a cyclopropyl group, a cyano groupand a tri(C₁ to C₃ alkyl)silyl group.} or the substituted pyrazolyloxygroup (The substituent is a benzoyl group substituted by two chlorineatoms, and two C₁ to C₃ alkyl groups.),

more preferably a chlorine atom, a bromine atom, trifluoromethyl groupor a cyano group,

still further preferably a chlorine atom or a bromine atom,

particularly preferably a chlorine atom.

(b) In the present invention, R² is preferably a hydrogen atom, afluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C₁ toC₃ alkyl group, a (C₁ to C₃ alkoxy)C₁ to C₃ alkyl group, a benzoyl groupwhich may be substituted {The substituent is the same or different 1 to2 substituent(s) selected from the group consisting of a fluorine atom,a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁ to C₃haloalkyl group (The halogen atom is the same or different 1 to 3halogen atom(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom.), a cyclopropyl group, a cyano groupand a tri(C₁ to C₃ alkyl)silyl group.}, a C₂ to C₄ alkoxycarbonyl group,a phenoxy group which may be substituted {The substituent is the same ordifferent 1 to 2 substituent(s) selected from the group consisting of afluorine atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group,a C₁ to C₃ haloalkyl group (The halogen atom is the same or different 1to 3 halogen atom(s) selected from the group consisting of a fluorineatom, a chlorine atom and a bromine atom.), a cyclopropyl group, a cyanogroup and a tri(C₁ to C₃ alkyl)silyl group.}, a phenylthio group whichmay be substituted {The substituent is the same or different 1 to 2substituent(s) selected from the group consisting of a fluorine atom, achlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁ to C₃haloalkyl group (The halogen atom is the same or different 1 to 3halogen atom(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom.), a cyclopropyl group, a cyano groupand a tri(C₁ to C₃ alkyl)silyl group.} or a tri(C₁ to C₃ alkyl)silylgroup,

more preferably a hydrogen atom, a fluorine atom, a chlorine atom, abromine atom, an iodine atom, a methyl group, an ethoxycarbonyl group ora trimethylsilyl group,

still further preferably a hydrogen atom.

(c) In the present invention, R³, R⁴, R⁵, R⁶ and R⁷ each independentlyrepresent preferably a hydrogen atom, a fluorine atom, a chlorine atom,a bromine atom, an iodine atom, a C₁ to C₄ alkyl group which may besubstituted (The substituent is the same or different 1 to 3substituent(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom, or a C₃ to C₄ cycloalkyl group, a C₁to C₃ alkylthio group or a C₁ to C₃ alkoxyimino group.), a C₂ to C₃alkenyl group, a C₂ to C₃ alkynyl group, a C₃ to C₅ cycloalkyl groupwhich may be substituted (The substituent is the same or different 1 to3 substituent(s) selected from the group consisting of a fluorine atom,a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₃ to C₄cycloalkyl group, a cyano group, a C₁ to C₃ alkoxy group and a C₁ to C₃alkylthio group.), a C₆ to C₇ bicycloalkyl group, a cyano group, a C₂ toC₄ alkylcarbonyl group, a C₂ to C₄ alkoxycarbonyl group, a phenyl groupwhich may be substituted {The substituent is a fluorine atom, a chlorineatom, a bromine atom, a C₁ to C₃ alkyl group or a C₁ to C₃ haloalkylgroup (The halogen atom is the same or different 1 to 3 halogen atom(s)selected from the group consisting of a fluorine atom, a chlorine atomand a bromine atom.).}, a 5- to 6-membered heterocyclic group which maybe substituted {the heterocycle contains one nitrogen atom, oxygen atomor sulfur atom in the ring, and may contain further 1 or 2 nitrogenatom(s). The substituent is the same or different 1 to 2 substituent(s)selected from the group consisting of a fluorine atom, a chlorine atom,a bromine atom, a C₁ to C₃ alkyl group and a C₁ to C₃ haloalkyl group(The halogen atom is the same or different 1 to 3 halogen atom(s)selected from the group consisting of a fluorine atom, a chlorine atomand a bromine atom.).}, a nitro group, a C₁ to C₃ alkoxy group, a C₁ toC₃ haloalkoxy group (The halogen atom is the same or different 1 to 3halogen atom(s) selected from the group consisting of a fluorine atom, achlorine atom and a bromine atom.), a phenoxy group which may besubstituted (The substituent is a pyridazinyloxy group substituted by asubstituent(s) selected frome the group consisting of a fluorine atom, achlorine atom, a bromine atom a C₁ to C₃ alkoxy group.) or a C₁ to C₃alkylthio group, or R³, R⁴, R⁵, R⁶ and R⁷ are a group(s) which is/areformed by the adjacent two of them with carbon atoms to which therespective substituents are bonded, and include a group represented byCH₂CH₂—, —CH₂CH₂CH₂—, —CH(CH₃)CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—,—OCH₂CH₂—, —OCH═CH—, —OCH═C(CH₃)—, —SCH═CH—, —N═CH—CH═CH—, —OCH₂O—,—OCH₂CH₂O—,

more preferably each independently represent a hydrogen atom, a fluorineatom, a chlorine atom, a bromine atom, an iodine atom, a C₁ to C₄ alkylgroup which may be substituted (The substituent is 1 to 3 fluorineatom(s), or a cyclopropyl group.), a C₃ to C₄ cycloalkyl group which maybe substituted (The substituent is the same 1 to 2 substituent selectedfrom the group consisting of a fluorine atom, a chlorine atom, a bromineatom, a C₁ to C₂ alkyl group, a cyclopropyl group and a C₁ to C₂ alkoxygroup.), a cyano group, C₂ to C₃ alkoxycarbonyl group, a nitro group, C₁to C₃ alkoxy group or trifluoromethoxy group, or, R³, R⁴, R⁵, R⁶ and R⁷are a group(s) which is/are formed by the adjacent two of them withcarbon atoms to which the respective substituents are bonded, andinclude a group represented by —CH₂CH₂CH₂—, —CH(CH₃)CH₂CH₂—, —OCH₂CH₂—,—OCH═CH— or

provided that R³ is not a hydrogen atom,

still further preferably each independently represent a hydrogen atom, afluorine atom, a chlorine atom, a bromine atom, an iodine atom, C₁ to C₃alkyl group, a C₃ to C₄ cycloalkyl group which may be substituted (Thesubstituent is the same 1 to 2 substituent(s) selected from the groupconsisting of a chlorine atom and a C₁ to C₂ alkyl group.), a cyanogroup or a C₁ to C₂ alkoxy group, or R³, R⁴, R⁵, R⁶ and R⁷ are agroup(s) which is/are formed by the adjacent two of them with carbonatoms to which the respective substituents are bonded, and include agroup represented by —CH₂CH₂CH₂— or —OCH═CH—, provided that R³ is not ahydrogen atom,

particularly preferably each independently represent a hydrogen atom, afluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methylgroup, an ethyl group, an isopropyl group, a cyclopropyl group which maybe substituted (The substituents are two chlorine atoms.) or a methoxygroup, or R³, R⁴, R⁵, R⁶ and R⁷ are a group(s) which is/are formed bythe adjacent two of them with carbon atoms to which the respectivesubstituents are bonded, and include a group represented by —CH₂CH₂CH₂—,provided that R³ is not a hydrogen atom,

most preferably R³ is a fluorine atom, a chlorine atom, a bromine atom,an iodine atom, a methyl group, an ethyl group, an isopropyl group, acyclopropyl group or a methoxy group

, and R⁷ is a hydrogen atom, a fluorine atom, a chlorine atom, a bromineatom, an iodine atom, a methyl group, an ethyl group, an isopropylgroup, a cyclopropyl group or methoxy group, and R⁴, R⁵ and R⁶ eachindependently represent a hydrogen atom or a methyl group.

(d) In the present invention, m and n are preferably both 0.

The compound (I) of the present invention is preferably a compoundwherein

-   (1a) R¹ is a hydrogen atom, a fluorine atom, a chlorine atom, a    bromine atom, a C₁ to C₃ alkyl group, a C₁ to C₃ haloalkyl group    (The halogen atom is 1 to 3 fluorine atom(s).), a cyclopropyl group,    a C₂ to C₃ alkenyl group, a cyano group, a C₂ to C₄ alkylcarbonyl    group, a di(C₁ to C₃ alkyl)carbamoyl group, a phenyl group which may    be substituted {The substituent is the same or different 1 to 2    substituent(s) selected from the group consisting of a fluorine    atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁    to C₃ haloalkyl group (The halogen atom is the same or different 1    to 3 halogen atom(s) selected from the group consisting of a    fluorine atom, a chlorine atom and a bromine atom.), a cyclopropyl    group, a cyano group and a tri(C₁ to C₃ alkyl)silyl group.}, a furyl    group, a thienyl group, a C₁ to C₃ alkoxy group, a phenoxy group    which may be substituted {The substituent is the same or different 1    to 2 substituent(s) selected from the group consisting of a fluorine    atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁    to C₃ haloalkyl group (The halogen atom is 1 to 3 fluorine    atom(s).), a cyclopropyl group, a cyano group and a tri(C₁ to C₃    alkyl)silyl group.} or the substituted pyrazolyloxy group (The    substituent is a benzoyl group substituted by two chlorine atoms and    two C₁ to C₃ alkyl groups.),-   (1b) R² is a hydrogen atom, a fluorine atom, a chlorine atom, a    bromine atom, an iodine atom, a C₁ to C₃ alkyl group, a (C₁ to C₃    alkoxy)C₁ to C₃ alkyl group, a benzoyl group which may be    substituted {The substituent is the same or different 1 to 2    substituent(s) selected from the group consisting of a fluorine    atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁    to C₃ haloalkyl group (The halogen atom is the same or different 1    to 3 halogen atom(s) selected from the group consisting of a    fluorine atom, a chlorine atom and a bromine atom.), a cyclopropyl    group, a cyano group and a tri(C₁ to C₃ alkyl)silyl group.}, a C₂ to    C₄ alkoxycarbonyl group, a phenoxy group which may be substituted    {The substituent is the same or different 1 to 2 substituent(s)    selected from the group consisting of a fluorine atom, a chlorine    atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁ to C₃ haloalkyl    group (The halogen atom is the same or different 1 to 3 halogen    atom(s) selected from the group consisting of a fluorine atom, a    chlorine atom and a bromine atom.), a cyclopropyl group, a cyano    group and a tri(C₁ to C₃ alkyl)silyl group.}, a phenylthio group    which may be substituted {The substituent is the same or different 1    to 2 substituent(s) selected from the group consisting of a fluorine    atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₁    to C₃ haloalkyl group (The halogen atom is the same or different 1    to 3 halogen atom(s) selected from the group consisting of a    fluorine atom, a chlorine atom and a bromine atom.), a cyclopropyl    group, a cyano group and a tri(C₁ to C₃ alkyl)silyl group.} or a    tri(C₁ to C₃ alkyl)silyl group,-   (1c) R³, R⁴, R⁵, R⁶ and R⁷ each independently represent a hydrogen    atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine    atom, a C₁ to C₄ alkyl group which may be substituted (The    substituent is the same or different 1 to 3 substituent(s) selected    from the group consisting of a fluorine atom, a chlorine atom and a    bromine atom, or a C₃ to C₄ cycloalkyl group, a C₁ to C₃ alkylthio    group or a C₁ to C₃ alkoxyimino group.), a C₂ to C₃ alkenyl group, a    C₂ to C₃ alkynyl group, a C₃ to C₅ cycloalkyl group which may be    substituted (The substituent is the same or different 1 to 3    substituent(s) selected from the group consisting of a fluorine    atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl group, a C₃    to C₄ cycloalkyl group, a cyano group, a C₁ to C₃ alkoxy group and a    C₁ to C₃ alkylthio group.), a C₆ to C₇ bicycloalkyl group, a cyano    group, a C₂ to C₄ alkylcarbonyl group, a C₂ to C₄ alkoxycarbonyl    group, a phenyl group which may be substituted {The substituent is a    fluorine atom, a chlorine atom, a bromine atom, a C₁ to C₃ alkyl    group or a C₁ to C₃ haloalkyl group (The halogen atom is the same or    different 1 to 3 halogen atom(s) selected from the group consisting    of a fluorine atom, a chlorine atom and a bromine atom.).}, a 5- to    6-membered heterocyclic group which may be substituted {the    heterocycle contains one nitrogen atom, oxygen atom or sulfur atom    in the ring, and may contain further 1 or 2 nitrogen atom(s). The    substituent is the same or different 1 to 2 substituent(s) selected    from the group consisting of a fluorine atom, a chlorine atom, a    bromine atom, a C₁ to C₃ alkyl group and a C₁ to C₃ haloalkyl group    (The halogen atom is the same or different 1 to 3 halogen atom(s)    selected from the group consisting of a fluorine atom, a chlorine    atom and a bromine atom.).}, a nitro group, a C₁ to C₃ alkoxy group,    a C₁ to C₃ haloalkoxy group (The halogen atom is the same or    different 1 to 3 halogen atom(s) selected from the group consisting    of a fluorine atom, a chlorine atom and a bromine atom.), a phenoxy    group which may be substituted (The substituent is a pyridazinyloxy    group substituted by a substituent(s) selected from the group    consisting of a fluorine atom, a chlorine atom, a bromine atom or a    C₁ to C₃ alkoxy group.) or C₁ to C₃ alkylthio group, or R³, R⁴, R⁵,    R⁶ and R⁷ are a group(s) which is/are formed by the adjacent two of    them with carbon atoms to which the respective substituents are    bonded, and include a group represented by —CH₂CH₂—, —CH₂CH₂CH₂—,    —CH(CH₃) CH₂CH₂—, —CH₂CH₂CH₂CH₂—, —CH═CH—CH═CH—, —OCH₂CH₂—,    —OCH═CH—, —OCH═C(CH₃)—, —SCH═CH—, —N═CH—CH═CH—, —OCH₂O—, —OCH₂CH₂O—,

-   (1d) m and n are both 0,

more preferably a compound wherein

-   (2a) R¹ is a chlorine atom, a bromine atom, a trifluoromethyl group    or a cyano group,-   (2b) R² is a hydrogen atom, a fluorine atom, a chlorine atom, a    bromine atom, an iodine atom, a methyl group, an ethoxycarbonyl    group or a trimethylsilyl group,-   (2c) R³, R⁴, R⁵, R⁶ and R⁷ each independently represent a hydrogen    atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine    atom, a C₁ to C₄ alkyl group which may be substituted (The    substituent is 1 to 3 fluorine atom(s), or a cyclopropyl group.), a    C₃ to C₄ cycloalkyl group which may be substituted (The substituent    is the same 1 to 2 substituent selected from the group consisting of    a fluorine atom, a chlorine atom, a bromine atom, a C₁ to C₂ alkyl    group, a cyclopropyl group and a C₁ to C₂ alkoxy group.), a cyano    group, a C₂ to C₃ alkoxycarbonyl group, a nitro group, a C₁ to C₃    alkoxy group or a trifluoromethoxy group, or R³, R⁴, R⁵, R⁶ and R⁷    are a group(s) which is/are formed by the adjacent two of them with    carbon atoms to which the respective substituents are bonded, and    include a group represented by —CH₂CH₂CH₂—, —CH(CH₃)CH₂CR₂—,    —OCH₂CH₂—, —OCH═CH— or

-    provided that R³ is not a hydrogen atom,-   (2d) m and n are both 0,

still further preferably a compound wherein

-   (3a) R¹ is a chlorine atom or a bromine atom,-   (3b) R² is a hydrogen atom,-   (3c) R³, R⁴, R⁵, R⁶ and R⁷ each independently represent a hydrogen    atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine    atom, C₁ to C₃ alkyl group, a C₃ to C₄ cycloalkyl group which may be    substituted (The substituent is the same 1 to 2 substituent(s)    selected from the group consisting of a chlorine atom and a C₁ to C₂    alkyl group.), a cyano group or a C₁ to C₂ alkoxy group, or R³, R⁴,    R⁵, R⁶ and R⁷ are a group(s) which is/are formed by the adjacent two    of them with carbon atoms to which the respective substituents are    bonded, and include a group represented by —CH₂CH₂CH₂— or —OCH═CH—,    provided that R³ is not a hydrogen atom,-   (3d) m and n are both 0,

particularly preferably a compound wherein

-   (4a) R¹ is a chlorine atom,-   (4b) R²is a hydrogen atom,-   (4c) R³, R⁴, R⁵, R⁶ and R⁷ each independently represent a hydrogen    atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine    atom, a methyl group, an ethyl group, an isopropyl group, a    cyclopropyl group which may be substituted (The substituents are two    chlorine atoms.) or a methoxy group, or R³, R⁴, R⁵, R⁶ and R⁷ are a    group(s) which is/are formed by the adjacent two of them with carbon    atoms to which the respective substituents are bonded, and include a    group represented by —CH₂CH₂CH₂—, provided that R³ is not a hydrogen    atom,-   (4d) m and n are both 0.

Representative compounds of the present invention are exemplified in thefollowing Table 1, but the present invention is not limited by thesecompounds.

In the following, in R³ to R⁷, “H” means that all the R³, R⁴, R⁵, R⁶ andR⁷ are hydrogen atoms, in R³ to R⁷, “2-Cl” means that R³ is a chlorineatom, “Me” represents a methyl group, “Et” represents an ethyl group,“Pr” represents a propyl group, “iPr” represents an isopropyl group,“cPr” represents a cyclopropyl group, “Bu” represents a butyl group,“iBu” represents an isobutyl group, “nsBu” represents a s-butyl group,“tBu” represents a tert-butyl group, “cBu” represents a cyclobutylgroup, “Pen” represents a pentyl group, “cPen” represents a cyclopentylgroup, “neoPen” represents a neopentyl group, “Hx” represents a hexylgroup, “cHx” represents a cyclohexyl group, in R³ to R⁷, “2-CH₂CH₂CH₂-3”means that R³ and R⁴ are a trimethylene group and form a 5-membered ringtogether with carbon atoms to which they are bonded, “═N—OMe” representsa methoxyimino group, “═O” represents a carbonyl group together withcarbon atom(s) to which they are bonded, “SO₂ (Ph-4-Me)” represents ap-tolylsulfonyl group, “cPr-1-F” represents a 1-fluorocyclopropyl group,“cPr-cis-2-(CH₂)₃-cis-3” represents a group represented by

“C(—CH₂CH₂—)—CH₂CH₂” represents a group represented by

“CH(CH₂)CH—CH₂” represents a group represented by

“CH(OCH₂)₂” represents a group represented by

“Fur” represents a furyl group, “Thi” represents a thienyl group, “Pyr”represents a pyridyl group, “Azr” represents a aziridinyl group, “Pyrd”represents a pyrrolidinyl group, “Pyrr” represents a pyrrolyl group,“Pyza” represents a pyrazolyl group, “Thiz” represents a thiazolylgroup, “Pyzn” represents a pyridazinyl group, “Np” represents a naphthylgroup, “1-Ad” represents a 1-adamantyl group, “Ioxa” represents anisoxazolyl group, “Tdia” represents a 1,2,3-thiadiazolyl group, “Bfur”represents a 1-benzofuranyl group, “Bthi” represents a 1-benzothienylgroup, “Bthia” represents a 1,3-benzothiazolyl group, “Boxaz” representsa 1,3-benzodioxolyl group, “Iqu” represents an isquinolyl group, “Azet”represents an azetidinyl group, “Ppri” represents a piperidyl group,“1-Ppri-4-OCH₂CH₂O-4” represents a group represented by the formula:

“Ppra” represents a piperadinyl group, “Morp” represents a morpholinylgroup, “Tmor” represents a thiomorpholinyl group, “Carb” represents acarbazolyl group, “Pthia” represents a phenothiazinyl group, “Thpy”represents a tetrahydro-2H-pyranyl group, “Q¹” represents an oxiranylgroup, “Q²” represents a benzoxazolyl group, “Q³” represents abenzothiazolyl group, “Q⁴” represents a fluorenyl group, “Q⁵” representsa 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl group, “Q⁶”represents a 6-chloro-3-(2-methylphenoxy)-4-pyridazinyl group, “Q⁷”represents a 6-chloro-3-(2-isopropylphenoxy)-4-pyridazinyl group, “Q⁸”represents a 6-chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl group, “Q⁹”represents a 6-chloro-3-(2,3-dihydro-1H-inden-4-yloxy)-4-pyridazinylgroup, “Q¹⁰” represents a 6-chloro-3-(2,6-dimethylphenoxy)-4-pyridazinylgroup, “Q¹¹” represents a6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl group, “Q^(l2)”represents a4-[2-chloro-3-(methoxycarbonyl)-4-(methylsulfonyl)benzoyl]-1-ethyl-1H-pyrazol-5-ylgroup, “Q¹³” represents a4-(2,4-dichloro-3-methylbenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl group,“Q¹⁴” represents a2-[2-chloro-4-(methylsulfonyl)benzoyl]-3-oxo-1-cyclohexen-1-yl group,“Q¹⁵” represents a2-[4-(methylsulfonyl)-2-nitrobenzoyl]-3-oxo-1-cyclohexen-1-yl group,“Q¹⁶” represents a2-cyano-1-cyclopropyl-3-[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]-3-oxo-1-propenylgroup, “Q¹⁷” represents a3-[4-chloro-2-(methylsulfonyl)phenyl]-2-cyano-1-cyclopropyl-3-oxo-1-propenylgroup, and “Q¹⁸” represents a 3,4-dihydro-2 (1H)-isoquinolinyl group,respectively.

TABLE 1

Compound No. R¹ R² X R³ to R⁷ m n 1 H H H H 0 0 2 H H H 2-Cl 0 0 3 H H H2-Br 0 0 4 H H H 2-I 0 0 5 H H H 2-Me 0 0 6 H H H 2-iPr 0 0 7 H H H2-cPr 0 0 8 H H H 2-cBu 0 0 9 H H H 2-CH₂CH₂CH₂-3 0 0 10 H H H2-cPr,5-Me 0 0 11 H H H 2-OMe,5-Me 0 0 12 H H H 2-F, 6-iPr 0 0 13 H H H2-Cl, 6-cPr 0 0 14 H H H 2-Br, 6-Me 0 0 15 H H H 2-I, 6-Me 0 0 16 H H H2, 6-Me₂ 0 0 17 H H H 2-Me, 6-Et 0 0 18 H H H 2-Me, 6-cPr 0 0 19 H H H2, 6-cPr₂ 0 0 20 H H H 2-cPr, 3,5-Me₂ 0 0 21 H H H 2-cPr, 5,6-Me₂ 0 0 22H H SO₂ (Ph-4-Me) 2-Cl 0 0 23 H H SO₂ (Ph-4-Me) 2-Br 0 0 24 H H SO₂(Ph-4-Me) 2-I 0 0 25 H H SO₂ (Ph-4-Me) 2-Me 0 0 26 H H SO₂ (Ph-4-Me)2-iPr 0 0 27 H H SO₂ (Ph-4-Me) 2-cPr 0 0 28 H H SO₂ (Ph-4-Me) 2-cBu 0 029 H H SO₂ (Ph-4-Me) 2-CH₂CH₂CH₂-3 0 0 30 H H SO₂ (Ph-4-Me) 2-cPr, 5-Me0 0 31 H H SO₂ (Ph-4-Me) 2-OMe, 5-Me 0 0 32 H H SO₂ (Ph-4-Me) 2-F, 6-iPr0 0 33 H H SO₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0 34 H H SO₂ (Ph-4-Me) 2-Br, 6-Me0 0 35 H H SO₂ (Ph-4-Me) 2-I, 6-Me 0 0 36 H H SO₂ (Ph-4-Me) 2, 6-Me₂ 0 037 H H SO₂ (Ph-4-Me) 2-Me, 6-Et 0 0 38 H H SO₂ (Ph-4-Me) 2-Me, 6-cPr 0 039 H H SO₂ (Ph-4-Me) 2, 6-cPr₂ 0 0 40 H H SO₂ (Ph-4-Me) 2-cPr, 3,5-Me₂ 00 41 H H SO₂ (Ph-4-Me) 2-cPr, 5, 6-Me₂ 0 0 42 H Cl H 2-Cl 0 0 43 H Cl H2-Br 0 0 44 H Cl H 2-I 0 0 45 H Cl H 2-Me 0 0 46 H Cl H 2-Et 0 0 47 H ClH 2-iPr 0 0 48 H Cl H 2-cPr 0 0 49 H Cl H 2-cBu 0 0 50 H Cl H2-CH₂CH₂CH₂-3 0 0 51 H Cl H 2-cPr, 5-Me 0 0 52 H Cl H 2-OMe, 5-Me 0 0 53H Cl H 2-F, 6-iPr 0 0 54 H Cl H 2-Cl, 6-cPr 0 0 55 H Cl H 2-Br, 6-Me 0 056 H Cl H 2-I, 6-Me 0 0 57 H Cl H 2, 6-Me₂ 0 0 58 H Cl H 2-Me, 6-Et 0 059 H Cl H 2-Me, 6-cPr 0 0 60 H Cl H 2,6-cPr₂ 0 0 61 H Cl H 2-cPr,3,5-Me₂ 0 0 62 H Cl H 2-cPr, 5, 6-Me₂ 0 0 63 H Cl SO₂ (Ph-4-Me) 2-Cl 0 064 H Cl SO₂ (Ph-4-Me) 2-Br 0 0 65 H Cl SO₂ (Ph-4-Me) 2-I 0 0 66 H Cl SO₂(Ph-4-Me) 2-Me 0 0 67 H Cl SO₂ (Ph-4-Me) 2-iPr 0 0 68 H Cl SO₂ (Ph-4-Me)2-cPr 0 0 69 H Cl SO₂ (Ph-4-Me) 2-cBu 0 0 70 H Cl SO₂ (Ph-4-Me)2-CH₂CH₂CH₂-3 0 0 71 H Cl SO₂ (Ph-4-Me) 2-cPr, 5-Me 0 0 72 H Cl SO₂(Ph-4-Me) 2-OMe, 5-Me 0 0 73 H Cl SO₂ (Ph-4-Me) 2-F, 6-iPr 0 0 74 H ClSO₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0 75 H Cl SO₂ (Ph-4-Me) 2-Br, 6-Me 0 0 76 HCl SO₂ (Ph-4-Me) 2-I, 6-Me 0 0 77 H Cl SO₂ (Ph-4-Me) 2,6-Me₂ 0 0 78 H ClSO₂ (Ph-4-Me) 2-Me, 6-Et 0 0 79 H Cl SO₂ (Ph-4-Me) 2-Me, 6-cPr 0 0 80 HCl SO₂ (Ph-4-Me) 2,6-cPr₂ 0 0 81 H Cl SO₂ (Ph-4-Me) 2-cPr, 3,5-Me₂ 0 082 H Cl SO₂ (Ph-4-Me) 2-cPr, 5, 6-Me₂ 0 0 83 H SiMe₃ H 2-Cl 0 0 84 HSiMe₃ H 2-Br 0 0 85 H SiMe₃ H 2-I 0 0 86 H SiMe₃ H 2-Me 0 0 87 H SiMe₃ H2-iPr 0 0 88 H SiMe₃ H 2-cPr 0 0 89 H SiMe₃ H 2-cBu 0 0 90 H SiMe₃ H2-CH₂CH₂CH₂-3 0 0 91 H SiMe₃ H 2-cPr, 5-Me 0 0 92 H SiMe₃ H 2-OMe, 5-Me0 0 93 H SiMe₃ H 2-F, 6-iPr 0 0 94 H SiMe₃ H 2-Cl, 6-cPr 0 0 95 H SiMe₃H 2-Br, 6-Me 0 0 96 H SiMe₃ H 2-I, 6-Me 0 0 97 H SiMe₃ H 2,6-Me₂ 0 0 98H SiMe₃ H 2-Me, 6-Et 0 0 99 H SiMe₃ H 2-Me, 6-cPr 0 0 100 H SiMe₃ H2,6-cPr₂ 0 0 101 H SiMe₃ H 2-cPr, 3,5-Me₂ 0 0 102 H SiMe₃ H 2-cPr,5,6-Me₂ 0 0 103 H SiMe₃ SO₂ (Ph-4-Me) 2-Cl 0 0 104 H SiMe₃ SO₂ (Ph-4-Me)2-Br 0 0 105 H SiMe₃ SO₂ (Ph-4-Me) 2-I 0 0 106 H SiMe₃ SO₂ (Ph-4-Me)2-Me 0 0 107 H SiMe₃ SO₂ (Ph-4-Me) 2-iPr 0 0 108 H SiMe₃ SO₂ (Ph-4-Me)2-cPr 0 0 109 H SiMe₃ SO₂ (Ph-4-Me) 2-cBu 0 0 110 H SiMe₃ SO₂ (Ph-4-Me)2-CH₂CH₂CH₂-3 0 0 111 H SiMe₃ SO₂ (Ph-4-Me) 2-cPr, 5-Me 0 0 112 H SiMe₃SO₂ (Ph-4-Me) 2-OMe, 5-Me 0 0 113 H SiMe₃ SO₂ (Ph-4-Me) 2-F, 6-iPr 0 0114 H SiMe₃ SO₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0 115 H SiMe₃ SO₂ (Ph-4-Me)2-Br, 6-Me 0 0 116 H SiMe₃ SO₂ (Ph-4-Me) 2-I, 6-Me 0 0 117 H SiMe₃ SO₂(Ph-4-Me) 2,6-Me₂ 0 0 118 H SiMe₃ SO₂ (Ph-4-Me) 2-Me, 6-Et 0 0 119 HSiMe₃ SO₂ (Ph-4-Me) 2-Me, 6-cPr 0 0 120 H SiMe₃ SO₂ (Ph-4-Me) 2,6-cPr₂ 00 121 H SiMe₃ SO₂ (Ph-4-Me) 2-cPr, 3,5-Me₂ 0 0 122 H SiMe₃ SO₂ (Ph-4-Me)2-cPr, 5,6-Me₂ 0 0 123 Cl H H H 0 0 124 Cl H H 2-F 0 0 125 Cl H H 2-Cl 00 126 Cl H H 2-Br 0 0 127 Cl H H 2-I 0 0 128 Cl H H 2-Me 0 0 129 Cl H H2-Me 1 0 130 Cl H H 2-Et 0 0 131 Cl H H 2-Pr 0 0 132 Cl H H 2-iPr 0 0133 Cl H H 2-Bu 0 0 134 Cl H H 2-iBu 0 0 135 Cl H H 2-sBu 0 0 136 Cl H H2-tBu 0 0 137 Cl H H 2-Pen 0 0 138 Cl H H 2-Hx 0 0 139 Cl H H 2-cPr 0 0140 Cl H H 2-(cPr-1-F) 0 0 141 Cl H H 2-(cPr-1-Cl) 0 0 142 Cl H H2-(cPr-1-Br) 0 0 143 Cl H H 2-(cPr-1-I) 0 0 144 Cl H H 2-(cPr-1-Me) 0 0145 Cl H H 2-(cPr-1-Et) 0 0 146 Cl H H 2-(cPr-1-Pr) 0 0 147 Cl H H2-(cPr-1-iPr) 0 0 148 Cl H H 2-(cPr-1-Bu) 0 0 149 Cl H H 2-(cPr-1-tBu) 00 150 Cl H H 2-(cPr-1-Hx) 0 0 151 Cl H H 2-(cPr-1-cPr) 0 0 152 Cl H H2-(cPr-1-cBu) 0 0 153 Cl H H 2-(cPr-1-cPen) 0 0 154 Cl H H2-(cPr-1-CH₂F) 0 0 155 Cl H H 2-(cPr-1-CH₂Cl) 0 0 156 Cl H H2-(cPr-1-CH₂Br) 0 0 157 Cl H H 2-(cPr-1-CHF₂) 0 0 158 Cl H H2-(cPr-1-CF₃) 0 0 159 Cl H H 2-(cPr-1-CCl₃) 0 0 160 Cl H H2-(cPr-1-CH₂CF₃) 0 0 161 Cl H H 2-(cPr-1-CH₂CCl₃) 0 0 162 Cl H H2-(cPr-1-CH═CH₂) 0 0 163 Cl H H 2-(cPr-1-CH₂OMe) 0 0 164 Cl H H2-(cPr-1-CH₂OEt) 0 0 165 Cl H H 2-(cPr-1-CH₂OiPr) 0 0 166 Cl H H2-(cPr-1-CH₂SMe) 0 0 167 Cl H H 2-(cPr-1-CH₂SEt) 0 0 168 Cl H H2-(cPr-1-CH₂S-iPr) 0 0 169 Cl H H 2-(cPr-1-CH₂SOMe) 0 0 170 Cl H H2-(cPr-1-CH₂SOEt) 0 0 171 Cl H H 2-(cPr-1-CH₂SO₂Me) 0 0 172 Cl H H2-(cPr-1-CH₂SO₂Et) 0 0 173 Cl H H 2-(cPr-1-CN) 0 0 174 Cl H H2-{cPr-1-C(═NOMe)Me} 0 0 175 Cl H H 2-(cPr-1-COMe) 0 0 176 Cl H H2-(cPr-1-COEt) 0 0 177 Cl H H 2-(cPr-1-COPh) 0 0 178 Cl H H2-(cPr-1-CO₂H) 0 0 179 Cl H H 2-(cPr-1-CO₂Me) 0 0 180 Cl H H2-(cPr-1-CO₂Et) 0 0 181 Cl H H 2-(cPr-1-CONH₂) 0 0 182 Cl H H2-(cPr-1-CONMe₂) 0 0 183 Cl H H 2-(cPr-1-CONEt₂) 0 0 184 Cl H H2-(cPr-1-Ph) 0 0 185 Cl H H 2-{cPr-1-(Ph-2-F)} 0 0 186 Cl H H2-{cPr-1-(Ph-2-Cl)} 0 0 187 Cl H H 2-{cPr-1-(Ph-2-Me)} 0 0 188 Cl H H2-{cPr-1-(Ph-4-Cl)} 0 0 189 Cl H H 2-{cPr-1-(Ph-4-Me)} 0 0 190 Cl H H2-{cPr-1-(2-Fur)} 0 0 191 Cl H H 2-{cPr-1-(2-Thi)} 0 0 192 Cl H H2-{cPr-1-(2-Pyr)} 0 0 193 Cl H H 2-(cPr-1-NH₂) 0 0 194 Cl H H2-(cPr-1-NHMe) 0 0 195 Cl H H 2-(cPr-1-NMe₂) 0 0 196 Cl H H2-(cPr-1-NHCOMe) 0 0 197 Cl H H 2-(cPr-1-NHCO₂Me) 0 0 198 Cl H H2-(cPr-1-NHCONMe₂) 0 0 199 Cl H H 2-(cPr-1-NHSO₂Me) 0 0 200 Cl H H2-(cPr-1-NO₂) 0 0 201 Cl H H 2-(cPr-1-OH) 0 0 202 Cl H H 2-(cPr-1-OMe) 00 203 Cl H H 2-(cPr-1-OEt) 0 0 204 Cl H H 2-(cPr-1-OCF₃) 0 0 205 Cl H H2-(cPr-1-OPh) 0 0 206 Cl H H 2-(cPr-1-SMe) 0 0 207 Cl H H 2-(cPr-1-SEt)0 0 208 Cl H H 2-(cPr-1-SPh) 0 0 209 Cl H H 2-(cPr-1-SOMe) 0 0 210 Cl HH 2-(cPr-1-SOEt) 0 0 211 Cl H H 2-(cPr-1-SO₂Me) 0 0 212 Cl H H2-(cPr-1-SO₂Et) 0 0 213 Cl H H 2-(cPr-2-F) 0 0 214 Cl H H 2-(cPr-2-Cl) 00 215 Cl H H 2-(cPr-2-Br) 0 0 216 Cl H H 2-(cPr-2-I) 0 0 217 Cl H H2-(cPr-2-Me) 0 0 218 Cl H H 2-(cPr-2-Et) 0 0 219 Cl H H 2-(cPr-2-Pr) 0 0220 Cl H H 2-(cPr-2-iPr) 0 0 221 Cl H H 2-(cPr-2-Bu) 0 0 222 Cl H H2-(cPr-2-tBu) 0 0 223 Cl H H 2-(cPr-2-Hx) 0 0 224 Cl H H 2-(cPr-2-cPr) 00 225 Cl H H 2-(cPr-2-CF₃) 0 0 226 Cl H H 2-(cPr-2-CN) 0 0 227 Cl H H2-(cPr-2-CH₂OMe) 0 0 228 Cl H H 2-(cPr-2-CH₂OEt) 0 0 229 Cl H H2-{cPr-2-C(═NOMe)Me} 0 0 230 Cl H H 2-(cPr-2-COMe) 0 0 231 Cl H H2-(cPr-2-COEt) 0 0 232 Cl H H 2-(cPr-2-COPh) 0 0 233 Cl H H2-(cPr-2-CO₂H) 0 0 234 Cl H H 2-(cPr-2-CO₂Me) 0 0 235 Cl H H2-(cPr-2-CO₂Et) 0 0 236 Cl H H 2-(cPr-2-CONH₂) 0 0 237 Cl H H2-(cPr-2-CONMe₂) 0 0 238 Cl H H 2-(cPr-2-CONEt₂) 0 0 239 Cl H H2-(cPr-2-NH₂) 0 0 240 Cl H H 2-(cPr-2-NHMe) 0 0 241 Cl H H2-(cPr-2-NMe₂) 0 0 242 Cl H H 2-(cPr-2-NHCOMe) 0 0 243 Cl H H2-(cPr-2-NHCO₂Me) 0 0 244 Cl H H 2-(cPr-2-NHCONMe₂) 0 0 245 Cl H H2-(cPr-2-NHSO₂Me) 0 0 246 Cl H H 2-(cPr-2-NO₂) 0 0 247 Cl H H2-(cPr-2-OH) 0 0 248 Cl H H 2-(cPr-2-OMe) 0 0 249 Cl H H 2-(cPr-2-OEt) 00 250 Cl H H 2-(cPr-2-OCF₃) 0 0 251 Cl H H 2-(cPr-2-OPh) 0 0 252 Cl H H2-(cPr-2-SMe) 0 0 253 Cl H H 2-(cPr-2-SEt) 0 0 254 Cl H H 2-(cPr-2-SPh)0 0 255 Cl H H 2-(cPr-2-SOMe) 0 0 256 Cl H H 2-(cPr-2-SOEt) 0 0 257 Cl HH 2-(cPr-2-SO₂Me) 0 0 258 Cl H H 2-(cPr-2-SO₂Et) 0 0 259 Cl H H2-(cPr-1,2-Me₂) 0 0 260 Cl H H 2-(cPr-1-Me-2-Et) 0 0 261 Cl H H2-(cPr-1-Et-2-Me) 0 0 262 Cl H H 2-(cPr-1,2-Et₂) 0 0 263 Cl H H2-{cPr-1,2-(CN)₂} 0 0 264 Cl H H 2-(cPr-2,2-F₂) 0 0 265 Cl H H2-(cPr-2,2-Cl₂) 0 0 266 Cl H H 2-(cPr-2,2-Br₂) 0 0 267 Cl H H2-(cPr-2,2-Me₂) 0 0 268 Cl H H 2-{cPr-2,2-(CN)₂} 0 0 269 Cl H H2-(cPr-2-cis-3-cis-Me₂) 0 0 270 Cl H H 2-(cPr-2-cis-3-trans-Me₂) 0 0 271Cl H H 2-(cPr-2-trans-3-trans-Me₂) 0 0 272 Cl H H2-{cPr-cis-2-(CH₂)₃-cis-3} 0 0 273 Cl H H 2-{cPr-trans-2-(CH₂)₃-trans-3}0 0 274 Cl H H 2-{cPr-cis-2-(CH₂)₄-cis-3} 0 0 275 Cl H H2-(cPr-trans-2-(CH₂)₄-trans-3) 0 0 276 Cl H H 2-{cPr-2,3-(CN)₂} 0 0 277Cl H H 2-(cPr-1,2,2-Me₃) 0 0 278 Cl H H 2-(cPr-1,2,3-Me₃) 0 0 279 Cl H H2-(cPr-2,2,3-cis-Me₃) 0 0 280 Cl H H 2-(cPr-2,2,3-trans-Me₃) 0 0 281 ClH H 2-(cPr-1,2,2,3-Me₄) 0 0 282 Cl H H 2-(cPr-2,2,3,3-Me₄) 0 0 283 Cl HH 2-(cPr-1,2,2,3,3-Me5) 0 0 284 Cl H H 2-cBu 0 0 285 Cl H H 2-(cBu-1-Me)0 0 286 Cl H H 2-(cBu-1-CH═CH₂) 0 0 287 Cl H H 2-(cBu-1-CN) 0 0 288 Cl HH 2-(cBu-1-CO₂H) 0 0 289 Cl H H 2-(cBu-1-COMe) 0 0 290 Cl H H2-(cBu-1-CO₂Me) 0 0 291 Cl H H 2-(cBu-1-NH₂) 0 0 292 Cl H H 2-cPen 0 0293 Cl H H 2-cHx 0 0 294 Cl H H 2-CH₂F 0 0 295 Cl H H 2-CH₂Cl 0 0 296 ClH H 2-CH₂Br 0 0 297 Cl H H 2-CHF₂ 0 0 298 Cl H H 2-CHCl₂ 0 0 299 Cl H H2-CHBr₂ 0 0 300 Cl H H 2-CF₃ 0 0 301 Cl H H 2-CCl₃ 0 0 302 Cl H H 2-CBr₃0 0 303 Cl H H 2-CH═CH₂ 0 0 304 Cl H H 2-CMe═CH₂ 0 0 305 Cl H H2-CH═CHMe 0 0 306 Cl H H 2-CH═CHCN 0 0 307 Cl H H 2-CH₂CH═CH₂ 0 0 308 ClH H 2-C CH 0 0 309 Cl H H 2-C CMe 0 0 310 Cl H H 2-C CSiMe₃ 0 0 311 Cl HH 2-CH₂cPr 0 0 312 Cl H H 2-CH₂cBu 0 0 313 Cl H H 2-CH₂cPen 0 0 314 Cl HH 2-CH₂cHx 0 0 315 Cl H H 2-CH₂Ph 0 0 316 Cl H H 2-CH₂CN 0 0 317 Cl H H2-CHMeCN 0 0 318 Cl H H 2-CMe₂CN 0 0 319 Cl H H 2-CH₂COMe 0 0 320 Cl H H2-CH₂CO₂Me 0 0 321 Cl H H 2-CHMeCO₂Me 0 0 322 Cl H H 2-CH₂CO₂Et 0 0 323Cl H H 2-CHMeCO₂Et 0 0 324 Cl H H 2-CH₂OMe 0 0 325 Cl H H 2-CH₂OEt 0 0326 Cl H H 2-CH₂SMe 0 0 327 Cl H H 2-CH₂SO₂Et 0 0 328 Cl H H 2-CH(OMe)₂0 0 329 Cl H H 2-CH(OCH₂)₂ 0 0 330 Cl H H 2-CN 0 0 331 Cl H H 2-CH═NOH 00 332 Cl H H 2-CH═NOMe 0 0 333 Cl H H 2-CMe═NOH 0 0 334 Cl H H2-CMe═NOMe 0 0 335 Cl H H 2-CHO 0 0 336 Cl H H 2-COMe 0 0 337 Cl H H2-COtBu 0 0 338 Cl H H 2-COPh 0 0 339 Cl H H 2-CO₂Me 0 0 340 Cl H H2-CO₂tBu 0 0 341 Cl H H 2-CO₂H 0 0 342 Cl H H 2-CONH₂ 0 0 343 Cl H H2-CONMe₂ 0 0 344 Cl H H 2-Ph 0 0 345 Cl H H 2-(Ph-2-Cl) 0 0 346 Cl H H2-(Ph-2-Me) 0 0 347 Cl H H 2-(Ph-2-CF₃) 0 0 348 Cl H H 2-(Ph-3-CF₃) 0 0(Isomer A) 349 Cl H H 2-(Ph-3-CF₃) 0 0 (Isomer B) 350 Cl H H 2-(1-Azr) 00 351 Cl H H 2-(2-Azr) 0 0 352 Cl H H 2-{2-Azr-1-SO₂—(Ph-4-Me)} 0 0 353Cl H H 2-(2-Q¹-2-Me) 0 0 354 Cl H H 2-(2-Q¹-3-Me) 0 0 355 Cl H H2-(1-Pyrd) 0 0 356 Cl H H 2-(1-Pyrr) 0 0 357 Cl H H 2-(2-Fur) 0 0 358 ClH H 2-(3-Fur) 0 0 359 Cl H H 2-(2-Thi) 0 0 360 Cl H H 2-(2-Thi-3-Cl) 0 0361 Cl H H 2-(3-Thi) 0 0 362 Cl H H 2-(1-Pyza) 0 0 363 Cl H H2-(1-Pyza-3-Me) 0 0 364 Cl H H 2-(1-Pyza-3,5-Me₂) 0 0 365 Cl H H2-(1-Pyza-3-CF₃) 0 0 366 Cl H H 2-(1-Pyza-4-CF₃) 0 0 367 Cl H H2-(1-Pyza-5-CF₃) 0 0 368 Cl H H 2-(3-Pyza-1-SO₂NMe₂) 0 0 369 Cl H H2-(5-Pyza-1-SO₂NMe₂) 0 0 370 Cl H H 2-(2-Thiz-4-Me) 0 0 371 Cl H H2-(2-Pyr) 0 0 372 Cl H H 2-(3-Pyr) 0 0 373 Cl H H 2-(4-Pyr) 0 0 374 Cl HH 2-(1-Pyr-2-OH) 0 0 375 Cl H H 2-(2-Q²) 0 0 376 Cl H H 2-(2-Q³) 0 0 377Cl H H 2-NH₂ 0 0 378 Cl H H 2-NHMe 0 0 379 Cl H H 2-NMe₂ 0 0 380 Cl H H2-NHCOMe 0 0 381 Cl H H 2-NHCO₂Me 0 0 382 Cl H H 2-NHCONMe₂ 0 0 383 Cl HH 2-NO₂ 0 0 384 Cl H H 2-OH 0 0 385 Cl H H 2-OMe 0 0 386 Cl H H 2-OEt 00 387 Cl H H 2-OiPr 0 0 388 Cl H H 2-OtBu 0 0 389 Cl H H 2-OCH₂F 0 0 390Cl H H 2-OCHF₂ 0 0 391 Cl H H 2-OCF₃ 0 0 392 Cl H H 2-OCH₂CF₃ 0 0 393 ClH H 2-OCH₂CCl₃ 0 0 394 Cl H H 2-OCH₂OMe 0 0 395 Cl H H 2-OCH₂OEt 0 0 396Cl H H 2-OCH₂CH₂OMe 0 0 397 Cl H H 2-OCH₂CH₂OEt 0 0 398 Cl H H 2-OPh 0 0399 Cl H H 2-O(Ph-2-OH) 0 0 400 Cl H H 2-O{Ph-2-O(3-Pyzn-6-Cl-4-OEt)} 00 401 Cl H H 2-SMe 0 0 402 Cl H H 2-SEt 0 0 403 Cl H H 2-S-iPr 0 0 404Cl H H 2-SOMe 0 0 405 Cl H H 2-SOEt 0 0 406 Cl H H 2-SO₂Me 0 0 407 Cl HH 2-SO₂Et 0 0 408 Cl H H 2-SiMe₃ 0 0 409 Cl H H 3-F 0 0 410 Cl H H 3-Cl0 0 411 Cl H H 3-Br 0 0 412 Cl H H 3-I 0 0 413 Cl H H 3-Me 0 0 414 Cl HH 3-Et 0 0 415 Cl H H 3-iPr 0 0 416 Cl H H 3-tBu 0 0 417 Cl H H 3-cPr 00 418 Cl H H 3-CF₃ 0 0 419 Cl H H 3-(2-Fur) 0 0 420 Cl H H 3-CN 0 0 421Cl H H 3-CHO 0 0 422 Cl H H 3-COMe 0 0 423 Cl H H 3-CO₂Me 0 0 424 Cl H H3-NO₂ 0 0 425 Cl H H 3-OMe 0 0 426 Cl H H 4-F 0 0 427 Cl H H 4-Cl 0 0428 Cl H H 4-Br 0 0 429 Cl H H 4-I 0 0 430 Cl H H 4-Me 0 0 431 Cl H H4-Et 0 0 432 Cl H H 4-iPr 0 0 433 Cl H H 4-tBu 0 0 434 Cl H H 4-cPr 0 0435 Cl H H 4-OMe 0 0 436 Cl H H 4-SiMe₃ 0 0 437 Cl H H 2,3-F₂ 0 0 438 ClH H 2-F, 3-Cl 0 0 439 Cl H H 2-F, 3-Br 0 0 440 Cl H H 2-F, 3-Me 0 0 441Cl H H 2-F, 3-CF₃ 0 0 442 Cl H H 2-Cl, 3-F 0 0 443 Cl H H 2,3-Cl₂ 0 0444 Cl H H 2-Cl, 3-Br 0 0 445 Cl H H 2-Cl, 3-Me 0 0 446 Cl H H 2-Cl,3-CF₃ 0 0 447 Cl H H 2-Cl, 3-OMe 0 0 448 Cl H H 2-Br, 3-F 0 0 449 Cl H H2-Br, 3-Cl 0 0 450 Cl H H 2-Br, 3-Me 0 0 451 Cl H H 2-Br, 3-CF₃ 0 0 452Cl H H 2-Br, 3-OMe 0 0 453 Cl H H 2-Me, 3-F 0 0 454 Cl H H 2-Me, 3-Cl 00 455 Cl H H 2-Me, 3-Br 0 0 456 Cl H H 2,3-Me₂ 0 0 457 Cl H H 2-Me,3-CF₃ 0 0 458 Cl H H 2-Me, 3-NO₂ 0 0 459 Cl H H 2-Me, 3-OMe 0 0 460 Cl HH 2-Me, 3-O(3-Pyzn-6-Cl-4-OH) 0 0 461 Cl H H 2-Et, 3-F 0 0 462 Cl H H2-Et, 3-Cl 0 0 463 Cl H H 2-Et, 3-Br 0 0 464 Cl H H 2-Et, 3-Me 0 0 465Cl H H 2-iPr, 3-F 0 0 466 Cl H H 2-iPr, 3-Cl 0 0 467 Cl H H 2-iPr, 3-Me0 0 468 Cl H H 2-iPr, 3-Et 0 0 469 Cl H H 2-cPr, 3-F 0 0 470 Cl H H2-cPr, 3-Cl 0 0 471 Cl H H 2-cPr, 3-Br 0 0 472 Cl H H 2-cPr, 3-Me 0 0473 Cl H H 2-cPr, 3-Et 0 0 474 Cl H H 2-cPr, 3-CF₃ 0 0 475 Cl H H 2-cPr,3-CN 0 0 476 Cl H H 2-cPr, 3-CO₂Me 0 0 477 Cl H H 2-cPr, 3-NO₂ 0 0 478Cl H H 2-cPr, 3-OMe 0 0 479 Cl H H 2-cBu, 3-F 0 0 480 Cl H H 2-cBu, 3-Cl0 0 481 Cl H H 2-cBu, 3-Br 0 0 482 Cl H H 2-cBu, 3-Me 0 0 483 Cl H H2-CF₃, 3-F 0 0 484 Cl H H 2-CF₃, 3-Cl 0 0 485 Cl H H 2-CF₃, 3-Br 0 0 486Cl H H 2-CF₃, 3-Me 0 0 487 Cl H H 2-CN, 3-F 0 0 488 Cl H H 2-CN, 3-Cl 00 489 Cl H H 2-CN, 3-Br 0 0 490 Cl H H 2-CN, 3-Me 0 0 491 Cl H H2-CO₂Me, 3-F 0 0 492 Cl H H 2-CO₂Me, 3-Cl 0 0 493 Cl H H 2-CO₂Me, 3-Br 00 494 Cl H H 2-CO₂Me, 3-Me 0 0 495 Cl H H 2-NO₂, 3-F 0 0 496 Cl H H2-NO₂, 3-Cl 0 0 497 Cl H H 2-NO₂, 3-Br 0 0 498 Cl H H 2-NO₂, 3-Me 0 0499 Cl H H 2-OMe, 3-F 0 0 500 Cl H H 2-OMe, 3-Cl 0 0 501 Cl H H 2-OMe,3-Br 0 0 502 Cl H H 2-OMe, 3-Me 0 0 503 Cl H H 2-OMe, 3-OMe 0 0 504 Cl HH 2-CH₂-3 0 0 505 Cl H H 2-CH₂CH₂-3 0 0 506 Cl H H 2-CH₂CH₂CH₂-3 0 0 507Cl H H 2-CHMeCH₂CH₂-3 0 0 508 Cl H H 2-CH(OMe)CH₂CH₂-3 0 0 509 Cl H H2-CH₂CHMeCH₂-3 0 0 510 Cl H H 2-CH₂CH₂CHMe-3 0 0 511 Cl H H2-CMe₂CH₂CH₂-3 0 0 512 Cl H H 2-C(OMe)₂CH₂CH₂-3 0 0 513 Cl H H2-CH₂CMe₂CH₂-3 0 0 514 Cl H H 2-C(—CH₂CH₂—)—CH₂CH₂-3 0 0 515 Cl H H2-CH(CH₂)CH—CH₂-3 0 0 516 Cl H H 2-CH₂—CH(CH₂)CH-3 0 0 517 Cl H H2-C(═O)CH₂CH₂-3 0 0 518 Cl H H 2-CH₂C(═O)CH₂-3 0 0 519 Cl H H2-CH₂CH₂C(═O)-3 0 0 520 Cl H H 2-C(═NOMe)CH₂CH₂-3 0 0 521 Cl H H2-CH₂CH₂CH₂CH₂-3 0 0 522 Cl H H 2-CHMeCH₂CH₂CH₂-3 0 0 523 Cl H H2-CMe₂CH₂CH₂CH₂-3 0 0 524 Cl H H 2-C(—CH₂CH₂—)—CH₂CH₂CH₂-3 0 0 525 Cl HH 2-CH(CH₂)CH—CH₂CH₂-3 0 0 526 Cl H H 2-CH(OMe)CH₂CH₂CH₂-3 0 0 527 Cl HH 2-CH═CHCH═CH-3 0 0 528 Cl H H 2-CH₂CH₂O-3 0 0 529 Cl H H 2-CHMeCH₂O-30 0 530 Cl H H 2-CH₂CHMeO-3 0 0 531 Cl H H 2-CH═CH—O-3 0 0 532 Cl H H2-CMe═CH—O-3 0 0 533 Cl H H 2-CH═CMe-O-3 0 0 534 Cl H H 2-CH═CH—S-3 0 0535 Cl H H 2-N═CHCH═CH-3 0 0 (Isomer A) 536 Cl H H 2-N═CHCH═CH-3 0 0(Isomer B) 537 Cl H H 2-N═CH—O-3 0 0 538 Cl H H 2-N═CMe—O-3 0 0 539 Cl HH 2-OCH₂CH₂-3 0 0 540 Cl H H 2-OCMe₂CH₂-3 0 0 541 Cl H H 2-OCH═CH-3 0 0542 Cl H H 2-OCMe═CH-3 0 0 543 Cl H H 2-OCF₂O-3 0 0 544 Cl H H 2-OCH₂O-30 0 545 Cl H H 2-OCHMeO-3 0 0 546 Cl H H 2-OCMe₂O-3 0 0 547 Cl H H2-OCH₂CH₂O-3 0 0 548 Cl H H 2-OCH═N-3 0 0 549 Cl H H 2-OCMe═N-3 0 0 550Cl H H 2,4-F₂ 0 0 551 Cl H H 2-Cl, 4-F 0 0 552 Cl H H 2,4-Cl₂ 0 0 553 ClH H 2-Br, 4-F 0 0 554 Cl H H 2,4-Br₂ 0 0 555 Cl H H 2-Br, 4-Me 0 0 556Cl H H 2-Br, 4-tBu 0 0 557 Cl H H 2-Me, 4-F 0 0 558 Cl H H 2-Me, 4-Cl 00 559 Cl H H 2,4-Me₂ 0 0 560 Cl H H 2-Et, 4-F 0 0 561 Cl H H 2-Et, 4-Cl0 0 562 Cl H H 2-Et, 4-I 0 0 563 Cl H H 2-Et, 4-Me 0 0 564 Cl H H 2-iPr,4-F 0 0 565 Cl H H 2-iPr, 4-Cl 0 0 566 Cl H H 2-iPr, 4-Br 0 0 567 Cl H H2-tBu, 4-Me 0 0 568 Cl H H 2-cPr, 4-F 0 0 569 Cl H H 2-cPr, 4-Cl 0 0 570Cl H H 2-cPr, 4-Br 0 0 571 Cl H H 2-cPr, 4-Me 0 0 572 Cl H H 2-cPr, 4-Et0 0 573 Cl H H 2-cPr, 4-CF₃ 0 0 574 Cl H H 2-cPr, 4-CN 0 0 575 Cl H H2-cPr, 4-CO₂Me 0 0 576 Cl H H 2-cPr, 4-NO₂ 0 0 577 Cl H H 2-cPr, 4-OMe 00 578 Cl H H 2-cBu, 4-F 0 0 579 Cl H H 2-cBu, 4-Cl 0 0 580 Cl H H 2-cBu,4-Br 0 0 581 Cl H H 2-cBu, 4-Me 0 0 582 Cl H H 2-CF₃, 4-F 0 0 583 Cl H H2-CF₃, 4-Cl 0 0 584 Cl H H 2-CF₃, 4-Br 0 0 585 Cl H H 2-CF₃, 4-Me 0 0586 Cl H H 2-CN, 4-F 0 0 587 Cl H H 2-CN, 4-Cl 0 0 588 Cl H H 2-CN, 4-Br0 0 589 Cl H H 2-CN, 4-Me 0 0 590 Cl H H 2-CO₂Me, 4-F 0 0 591 Cl H H2-CO₂Me, 4-Cl 0 0 592 Cl H H 2-CO₂Me, 4-Br 0 0 593 Cl H H 2-CO₂Me, 4-Me0 0 594 Cl H H 2-NO₂, 4-F 0 0 595 Cl H H 2-NO₂, 4-Cl 0 0 596 Cl H H2-NO₂, 4-Br 0 0 597 Cl H H 2-NO₂, 4-Me 0 0 598 Cl H H 2-OMe, 4-F 0 0 599Cl H H 2-OMe, 4-Cl 0 0 600 Cl H H 2-OMe, 4-Br 0 0 601 Cl H H 2-OMe, 4-Me0 0 602 Cl H H 2,4-(OMe)₂ 0 0 603 Cl H H 2,5-F₂ 0 0 604 Cl H H 2-F, 5-Cl0 0 605 Cl H H 2-F, 5-Br 0 0 606 Cl H H 2-F, 5-I 0 0 607 Cl H H 2-F,5-Me 0 0 608 Cl H H 2-F, 5-CF₃ 0 0 609 Cl H H 2-F, 5-OMe 0 0 610 Cl H H2-Cl, 5-F 0 0 611 Cl H H 2,5-Cl₂ 0 0 612 Cl H H 2-Cl, 5-Br 0 0 613 Cl HH 2-Cl, 5-I 0 0 614 Cl H H 2-Cl, 5-Me 0 0 615 Cl H H 2-Cl, 5-CF₃ 0 0 616Cl H H 2-Cl, 5-OMe 0 0 617 Cl H H 2-Me, 5-F 0 0 618 Cl H H 2-Me, 5-Cl 00 619 Cl H H 2-Me, 5-Br 0 0 620 Cl H H 2-Me, 5-I 0 0 621 Cl H H 2,5-Me₂0 0 622 Cl H H 2-Me, 5-Et 0 0 623 Cl H H 2-Me, 5-iPr 0 0 624 Cl H H2-Me, 5-CF₃ 0 0 625 Cl H H 2-Me, 5-CN 0 0 626 Cl H H 2-Me, 5-CO₂H 0 0627 Cl H H 2-Me, 5-NH₂ 0 0 628 Cl H H 2-Me, 5-NMe₂ 0 0 629 Cl H H 2-Me,5-OMe 0 0 630 Cl H H 2-Et, 5-F 0 0 631 Cl H H 2-Et, 5-Cl 0 0 632 Cl H H2-Et, 5-Br 0 0 633 Cl H H 2-Et, 5-Me 0 0 634 Cl H H 2-Et, 5-CN 0 0 635Cl H H 2-Et, 5-OMe 0 0 636 Cl H H 2-iPr, 5-F 0 0 637 Cl H H 2-iPr, 5-Cl0 0 638 Cl H H 2-iPr, 5-Br 0 0 639 Cl H H 2-iPr, 5-I 0 0 640 Cl H H2-iPr, 5-Me 0 0 641 Cl H H 2-iPr, 5-Et 0 0 642 Cl H H 2-iPr, 5-iPr 0 0643 Cl H H 2-iPr, 5-CF₃ 0 0 644 Cl H H 2-iPr, 5-CN 0 0 645 Cl H H 2-iPr,5-OMe 0 0 646 Cl H H 2-tBu, 5-F 0 0 647 Cl H H 2-tBu, 5-Cl 0 0 648 Cl HH 2-tBu, 5-Br 0 0 649 Cl H H 2-tBu, 5-I 0 0 650 Cl H H 2-tBu, 5-Me 0 0651 Cl H H 2-tBu, 5-Et 0 0 652 Cl H H 2-tBu, 5-iPr 0 0 653 Cl H H 2-tBu,5-tBu 0 0 654 Cl H H 2-tBu, 5-cPr 0 0 655 Cl H H 2-tBu, 5-CF₃ 0 0 656 ClH H 2-tBu, 5-CN 0 0 657 Cl H H 2-tBu, 5-OMe 0 0 658 Cl H H 2-cPr, 5-F 00 659 Cl H H 2-cPr, 5-Cl 0 0 660 Cl H H 2-cPr, 5-Br 0 0 661 Cl H H2-cPr, 5-I 0 0 662 Cl H H 2-cPr, 5-Me 0 0 663 Cl H H 2-cPr, 5-Et 0 0 664Cl H H 2-cPr, 5-iPr 0 0 665 Cl H H 2-cPr, 5-tBu 0 0 666 Cl H H 2-cPr,5-CF₃ 0 0 667 Cl H H 2-cPr, 5-CN 0 0 668 Cl H H 2-cPr, 5-OMe 0 0 669 ClH H 2-CF₃, 5-F 0 0 670 Cl H H 2-CF₃, 5-Cl 0 0 671 Cl H H 2-CF₃, 5-Br 0 0672 Cl H H 2-CF₃, 5-I 0 0 673 Cl H H 2-CF₃, 5-Me 0 0 674 Cl H H 2-CF₃,5-CN 0 0 675 Cl H H 2-CF₃, 5-OMe 0 0 676 Cl H H 2-CH═CH₂, 5-F 0 0 677 ClH H 2-CH═CH₂, 5-Cl 0 0 678 Cl H H 2-CHCH₂, 5-Me 0 0 679 Cl H H 2-C═CHMe,5-F 0 0 680 Cl H H 2-CH═CHMe, 5-Cl 0 0 681 Cl H H 2-CH═CHMe, 5-Me 0 0682 Cl H H 2-CMe═CH₂, 5-F 0 0 683 Cl H H 2-CMe═CH₂, 5-Cl 0 0 684 Cl H H2-CMe═CH₂, 5-Me 0 0 685 Cl H H 2-CN, 5-F 0 0 686 Cl H H 2-CN, 5-Cl 0 0687 Cl H H 2-CN, 5-Br 0 0 688 Cl H H 2-CN, 5-I 0 0 689 Cl H H 2-CN, 5-Me0 0 690 Cl H H 2-CN, 5-CN 0 0 691 Cl H H 2-CN, 5-OMe 0 0 692 Cl H H2-CHO, 5-NMe₂ 0 0 693 Cl H H 2-CO₂Me, 5-F 0 0 694 Cl H H 2-CO₂Me, 5-Cl 00 695 Cl H H 2-CO₂Me, 5-Br 0 0 696 Cl H H 2-CO₂Me, 5-I 0 0 697 Cl H H2-CO₂Me, 5-Me 0 0 698 Cl H H 2-CO₂Me, 5-CN 0 0 699 Cl H H 2-CO₂Me, 5-OMe0 0 700 Cl H H 2-OMe, 5-F 0 0 701 Cl H H 2-OMe, 5-Cl 0 0 702 Cl H H2-OMe, 5-Br 0 0 703 Cl H H 2-OMe, 5-I 0 0 704 Cl H H 2-OMe, 5-Me 0 0 705Cl H H 2-OMe, 5-Et 0 0 706 Cl H H 2-OMe, 5-CF₃ 0 0 707 Cl H H 2-OMe,5-CN 0 0 708 Cl H H 2-OMe, 5-NO₂ 0 0 709 Cl H H 2-OMe, 5-OMe 0 0 710 ClH H 2,6-F₂ 0 0 711 Cl H H 2-F, 6-Cl 0 0 712 Cl H H 2-F, 6-Br 0 0 713 ClH H 2-F, 6-I 0 0 714 Cl H H 2-F, 6-Me 0 0 715 Cl H H 2-F, 6-Et 0 0 716Cl H H 2-F, 6-Pr 0 0 717 Cl H H 2-F, 6-iPr 0 0 718 Cl H H 2-F, 6-tBu 0 0719 Cl H H 2-F, 6-cPr 0 0 720 Cl H H 2-F, 6-cBu 0 0 721 Cl H H 2-F,6-cPen 0 0 722 Cl H H 2-F, 6-CF₃ 0 0 723 Cl H H 2-F, 6-CH₂OMe 0 0 724 ClH H 2-F, 6-CH₂OEt 0 0 725 Cl H H 2-F, 6-CH₂CH₂OMe 0 0 726 Cl H H 2-F,6-CH₂SMe 0 0 727 Cl H H 2-F, 6-CH₂SEt 0 0 728 Cl H H 2-F, 6-CHMeSEt 0 0729 Cl H H 2-F, 6-CN 0 0 730 Cl H H 2-F, 6-CO₂Me 0 0 731 Cl H H 2-F,6-NO₂ 0 0 732 Cl H H 2-F, 6-OMe 0 0 733 Cl H H 2,6-Cl₂ 0 0 734 Cl H H2-Cl, 6-Br 0 0 735 Cl H H 2-Cl, 6-I 0 0 736 Cl H H 2-Cl, 6-Me 0 0 737 ClH H 2-Cl, 6-Et 0 0 738 Cl H H 2-Cl, 6-iPr 0 0 739 Cl H H 2-Cl, 6-tBu 0 0740 Cl H H 2-Cl, 6-cPr 0 0 741 Cl H H 2-Cl, 6-cBu 0 0 742 Cl H H 2-Cl,6-cPen 0 0 743 Cl H H 2-Cl, 6-CF₃ 0 0 744 Cl H H 2-Cl, 6-CH═CH₂ 0 0 745Cl H H 2-Cl, 6-CH₂CH═CH₂ 0 0 746 Cl H H 2-Cl, 6-CH₂CMe═CH₂ 0 0 747 Cl HH 2-Cl, 6-CH₂OMe 0 0 748 Cl H H 2-Cl, 6-CH₂OEt 0 0 749 Cl H H 2-Cl,6-CH₂CH₂OMe 0 0 750 Cl H H 2-Cl, 6-CH₂SMe 0 0 751 Cl H H 2-Cl, 6-CH₂SEt0 0 752 Cl H H 2-Cl, 6-CN 0 0 753 Cl H H 2-Cl, 6-CO₂Me 0 0 754 Cl H H2-Cl, 6-NO₂ 0 0 755 Cl H H 2-Cl, 6-OMe 0 0 756 Cl H H 2,6-Br₂ 0 0 757 ClH H 2-Br, 6-I 0 0 758 Cl H H 2-Br, 6-Me 0 0 759 Cl H H 2-Br, 6-Et 0 0760 Cl H H 2-Br, 6-iPr 0 0 761 Cl H H 2-Br, 6-tBu 0 0 762 Cl H H 2-Br,6-cPr 0 0 763 Cl H H 2-Br, 6-cBu 0 0 764 Cl H H 2-Br, 6-cPen 0 0 765 ClH H 2-Br, 6-cHx 0 0 766 Cl H H 2-Br, 6-CF₃ 0 0 767 Cl H H 2-Br, 6-CH═CH₂0 0 768 Cl H H 2-Br, 6-CH₂CH═CH₂ 0 0 769 Cl H H 2-Br, 6-CH₂CMe═CH₂ 0 0770 Cl H H 2-Br, 6-CH₂OMe 0 0 771 Cl H H 2-Br, 6-CH₂OEt 0 0 772 Cl H H2-Br, 6-CH₂CH₂OMe 0 0 773 Cl H H 2-Br, 6-CH₂SMe 0 0 774 Cl H H 2-Br,6-CH₂SEt 0 0 775 Cl H H 2-Br, 6-CN 0 0 776 Cl H H 2-Br, 6-CO₂Me 0 0 777Cl H H 2-Br, 6-NO₂ 0 0 778 Cl H H 2-Br, 6-OMe 0 0 779 Cl H H 2,6-I₂ 0 0780 Cl H H 2-I, 6-Me 0 0 781 Cl H H 2-I, 6-Et 0 0 782 Cl H H 2-I, 6-iPr0 0 783 Cl H H 2-I, 6-tBu 0 0 784 Cl H H 2-I, 6-cPr 0 0 785 Cl H H 2-I,6-cBu 0 0 786 Cl H H 2-I, 6-cPen 0 0 787 Cl H H 2-I, 6-cHx 0 0 788 Cl HH 2-I, 6-CF₃ 0 0 789 Cl H H 2-I, 6-CH═CH₂ 0 0 790 Cl H H 2-I,6-CH₂CH═CH₂ 0 0 791 Cl H H 2-I, 6-CH₂CMe═CH₂ 0 0 792 Cl H H 2-I,6-CH₂OMe 0 0 793 Cl H H 2-I, 6-CH₂OEt 0 0 794 Cl H H 2-I, 6-CH₂CH₂OMe 00 795 Cl H H 2-I, 6-CH₂SMe 0 0 796 Cl H H 2-I, 6-CH₂SEt 0 0 797 Cl H H2-I, 6-CN 0 0 798 Cl H H 2-I, 6-CO₂Me 0 0 799 Cl H H 2-I, 6-NO₂ 0 0 800Cl H H 2-I, 6-OMe 0 0 801 Cl H H 2,6-Me₂ 0 0 802 Cl H H 2-Me, 6-Et 0 0803 Cl H H 2-Me, 6-iPr 0 0 804 Cl H H 2-Me, 6-sBu 0 0 805 Cl H H 2-Me,6-tBu 0 0 806 Cl H H 2-Me, 6-cPr 0 0 807 Cl H H 2-Me, 6-(cPr-1-F) 0 0808 Cl H H 2-Me, 6-(cPr-1-Cl) 0 0 809 Cl H H 2-Me, 6-(cPr-1-Br) 0 0 810Cl H H 2-Me, 6-(cPr-1-I) 0 0 811 Cl H H 2-Me, 6-(cPr-1-Me) 0 0 812 Cl HH 2-Me, 6-(cPr-1-Et) 0 0 813 Cl H H 2-Me, 6-(cPr-1-cPr) 0 0 814 Cl H H2-Me, 6-(cPr-1-CN) 0 0 815 Cl H H 2-Me, 6-(cPr-1-OMe) 0 0 816 Cl H H2-Me, 6-(cPr-1-OEt) 0 0 817 Cl H H 2-Me, 6-(cPr-2-Me) 0 0 818 Cl H H2-Me, 6-(cPr-2-Et) 0 0 819 Cl H H 2-Me, 6-(cPr-2-CN) 0 0 820 Cl H H2-Me, 6-(cPr-2-OMe) 0 0 821 Cl H H 2-Me, 6-(cPr-2-OEt) 0 0 822 Cl H H2-Me, 6-(cPr-2-OCF₃) 0 0 823 Cl H H 2-Me, 6-(cPr-1,2-Me₂) 0 0 824 Cl H H2-Me, 6-{cPr-1,2-(CN)₂} 0 0 825 Cl H H -Me, 6-(cPr-2,2-Me₂) 0 0 826 Cl HH 2-Me, 6-(cPr-2,2-F₂) 0 0 827 Cl H H 2-Me, 6-(cPr-2,2-Cl₂) 0 0 828 Cl HH 2-Me, 6-(cPr-2,2-Br₂) 0 0 829 Cl H H 2-Me, 6-{cPr-2,2-(CN)₂} 0 0 830Cl H H 2-Me, 6-cBu 0 0 831 Cl H H 2-Me, 6-cPen 0 0 832 Cl H H 2-Me,6-cHx 0 0 833 Cl H H 2-Me, 6-CF₃ 0 0 834 Cl H H 2-Me, 6-CH═CH₂ 0 0 835Cl H H 2-Me, 6-CH₂CH═CH₂ 0 0 836 Cl H H 2-Me, 6-CH═CH—NO₂ 0 0 837 Cl H H2-Me, 6-CH₂OMe 0 0 838 Cl H H 2-Me, 6-CH₂OEt 0 0 839 Cl H H 2-Me,6-CH₂CH₂OMe 0 0 840 Cl H H 2-Me, 6-CH₂SMe 0 0 841 Cl H H 2-Me, 6-CH₂SEt0 0 842 Cl H H 2-Me, 6-CN 0 0 843 Cl H H 2-Me, 6-CO₂Me 0 0 844 Cl H H2-Me, 6-NO₂ 0 0 845 Cl H H 2-Me, 6-OMe 0 0 846 Cl H H 2,6-Et2 0 0 847 ClH H 2-Et, 6-iPr 0 0 848 Cl H H 2-Et, 6-sBu 0 0 849 Cl H H 2-Et, 6-tBu 00 850 Cl H H 2-Et, 6-cPr 0 0 851 Cl H H 2-Et, 6-(cPr-1-F) 0 0 852 Cl H H2-Et, 6-(cPr-1-Cl) 0 0 853 Cl H H 2-Et, 6-(cPr-1-Br) 0 0 854 Cl H H2-Et, 6-(cPr-1-I) 0 0 855 Cl H H 2-Et, 6-(cPr-1-Me) 0 0 856 Cl H H 2-Et,6-(cPr-1-Et) 0 0 857 Cl H H 2-Et, 6-(cPr-1-cPr) 0 0 858 Cl H H 2-Et,6-(cPr-1-CN) 0 0 859 Cl H H 2-Et, 6-(cPr-1-OMe) 0 0 860 Cl H H 2-Et,6-(cPr-1-OEt) 0 0 861 Cl H H 2-Et, 6-(cPr-2-Me) 0 0 862 Cl H H 2-Et,6-(cPr-2-Et) 0 0 863 Cl H H 2-Et, 6-(cPr-2-CN) 0 0 864 Cl H H 2-Et,6-(cPr-2-OMe) 0 0 865 Cl H H 2-Et, 6-(cPr-2-OEt) 0 0 866 Cl H H 2-Et,6-(cPr-2-OCF₃) 0 0 867 Cl H H 2-Et, 6-(cPr-1,2-Me₂) 0 0 868 Cl H H 2-Et,6-{cPr-1,2-(CN)₂} 0 0 869 Cl H H 2-Et, 6-(cPr-2,2-Me₂) 0 0 870 Cl H H2-Et, 6-(cPr-2,2-F₂) 0 0 871 Cl H H 2-Et, 6-(cPr-2,2-Cl₂) 0 0 872 Cl H H2-Et, 6-(cPr-2,2-Br₂) 0 0 873 Cl H H 2-Et, 6-{cPr-2,2-(CN)₂} 0 0 874 ClH H 2-Et, 6-cBu 0 0 875 Cl H H 2-Et, 6-cPen 0 0 876 Cl H H 2-Et, 6-cHx 00 877 Cl H H 2-Et, 6-CF₃ 0 0 878 Cl H H 2-Et, 6-CH═CH₂ 0 0 879 Cl H H2-Et, 6-CH₂CH═CH₂ 0 0 880 Cl H H 2-Et, 6-CH₂CMe═CH₂ 0 0 881 Cl H H 2-Et,6-CH₂OMe 0 0 882 Cl H H 2-Et, 6-CH₂OEt 0 0 883 Cl H H 2-Et, 6-CH₂CH₂OMe0 0 884 Cl H H 2-Et, 6-CH₂SMe 0 0 885 Cl H H 2-Et, 6-CH₂SEt 0 0 886 Cl HH 2-Et, 6-CN 0 0 887 Cl H H 2-Et, 6-CO₂Me 0 0 888 Cl H H 2-Et, 6-NO₂ 0 0889 Cl H H 2-Et, 6-OMe 0 0 890 Cl H H 2,6-Pr₂ 0 0 891 Cl H H 2-Pr, 6-iPr0 0 892 Cl H H 2-Pr, 6-tBu 0 0 893 Cl H H 2-Pr, 6-cPr 0 0 894 Cl H H2,6-iPr₂ 0 0 895 Cl H H 2-iPr, 6-tBu 0 0 896 Cl H H 2-iPr, 6-cPr 0 0 897Cl H H 2-iPr, 6-cBu 0 0 898 Cl H H 2-iPr, 6-cPen 0 0 899 Cl H H 2-iPr,6-cHx 0 0 900 Cl H H 2-iPr, 6-CF₃ 0 0 901 Cl H H 2-iPr, 6-CH═CH₂ 0 0 902Cl H H 2-iPr, 6-CH₂CH═CH₂ 0 0 903 Cl H H 2-iPr, 6-CH₂CMe═CH₂ 0 0 904 ClH H 2-iPr, 6-CH₂OMe 0 0 905 Cl H H 2-iPr, 6-CH₂OEt 0 0 906 Cl H H 2-iPr,6-CH₂CH₂OMe 0 0 907 Cl H H 2-iPr, 6-CH₂SMe 0 0 908 Cl H H 2-iPr,6-CH₂SEt 0 0 909 Cl H H 2-iPr, 6-CN 0 0 910 Cl H H 2-iPr, 6-CO₂Me 0 0911 Cl H H 2-iPr, 6-NO₂ 0 0 912 Cl H H 2-iPr, 6-OMe 0 0 913 Cl H H2,6-tBu₂ 0 0 914 Cl H H 2-tBu, 6-cPr 0 0 915 Cl H H 2-tBu, 6-cBu 0 0 916Cl H H 2-tBu, 6-cPen 0 0 917 Cl H H 2-tBu, 6-cHx 0 0 918 Cl H H 2-tBu,6-CF₃ 0 0 919 Cl H H 2-tBu, 6-CH═CH₂ 0 0 920 Cl H H 2-tBu, 6-CH₂CH═CH₂ 00 921 Cl H H 2-tBu, 6-CH₂CMe═CH₂ 0 0 922 Cl H H 2-tBu, 6-CH₂OMe 0 0 923Cl H H 2-tBu, 6-CH₂OEt 0 0 924 Cl H H 2-tBu, 6-CH₂CH₂OMe 0 0 925 Cl H H2-tBu, 6-CH₂SMe 0 0 926 Cl H H 2-tBu, 6-CH₂SEt 0 0 927 Cl H H 2-tBu,6-CN 0 0 928 Cl H H 2-tBu, 6-CO₂Me 0 0 929 Cl H H 2-tBu, 6-NO₂ 0 0 930Cl H H 2-tBu, 6-OMe 0 0 931 Cl H H 2,6-cPr₂ 0 0 932 Cl H H 2-cPr,6-(cPr-1-cPr) 0 0 933 Cl H H 2-cPr, 6-(cPr-1-CN) 0 0 934 Cl H H 2-cPr,6-(cPr-1-OMe) 0 0 935 Cl H H 2-cPr, 6-(cPr-1-OEt) 0 0 936 Cl H H 2-cPr,6-(cPr-2-Me) 0 0 937 Cl H H 2-cPr, 6-(cPr-2-Et) 0 0 938 Cl H H 2-cPr,6-(cPr-2-CN) 0 0 939 Cl H H 2-cPr, 6-(cPr-2-OMe) 0 0 940 Cl H H 2-cPr,6-(cPr-2-OEt) 0 0 941 Cl H H 2-cPr, 6-(cPr-2-OCF₃) 0 0 942 Cl H H 2-cPr,6-(cPr-1,2-Me₂) 0 0 943 Cl H H 2-cPr, 6-{cPr-1,2-(CN)₂} 0 0 944 Cl H H2-cPr, 6-(cPr-2,2-Me₂) 0 0 945 Cl H H 2-cPr, 6-(cPr-2,2-F₂) 0 0 946 Cl HH 2-cPr, 6-(cPr-2,2-Cl₂) 0 0 947 Cl H H 2-cPr, 6-(cPr-2,2-Br₂) 0 0 948Cl H H 2-cPr, 6-{cPr-2,2-(CN)₂} 0 0 949 Cl H H 2-cPr, 6-cBu 0 0 950 Cl HH 2-cPr, 6-cPen 0 0 951 Cl H H 2-cPr, 6-cHx 0 0 952 Cl H H 2-cPr, 6-CF₃0 0 953 Cl H H 2-cPr, 6-CH═CH₂ 0 0 954 Cl H H 2-cPr, 6-CH₂CH═CH₂ 0 0 955Cl H H 2-cPr, 6-CH₂CMe═CH₂ 0 0 956 Cl H H 2-cPr, 6-CH₂OMe 0 0 957 Cl H H2-cPr, 6-CH₂OEt 0 0 958 Cl H H 2-cPr, 6-CH₂CH₂OMe 0 0 959 Cl H H 2-cPr,6-CH₂SMe 0 0 960 Cl H H 2-cPr, 6-CH₂SEt 0 0 961 Cl H H 2-cPr, 6-CN 0 0962 Cl H H 2-cPr, 6-CO₂Me 0 0 963 Cl H H 2-cPr, 6-NO₂ 0 0 964 Cl H H2-cPr, 6-OMe 0 0 965 Cl H H 2-cPr, 6-OEt 0 0 966 Cl H H 2-cPr, 6-SMe 0 0967 Cl H H 2-CF₃, 6-CH═CH₂ 0 0 968 Cl H H 2-CF₃, 6-CH₂CH═CH₂ 0 0 969 ClH H 2-CF₃, 6-CH₂CMe═CH₂ 0 0 970 Cl H H 2-CF₃, 6-CH₂OMe 0 0 971 Cl H H2-CF₃, 6-CH₂OEt 0 0 972 Cl H H 2-CF₃, 6-CH₂CH₂OMe 0 0 973 Cl H H 2-CF₃,6-CH₂SMe 0 0 974 Cl H H 2-CF₃, 6-CH₂SEt 0 0 975 Cl H H 2-CF₃, 6-CN 0 0976 Cl H H 2-CF₃, 6-CO₂Me 0 0 977 Cl H H 2-CF₃, 6-NO₂ 0 0 978 Cl H H2-CF₃, 6-OMe 0 0 979 Cl H H 2,6-(CH═CHMe)₂ 0 0 980 Cl H H 2-CH═CHMe,6-CN 0 0 981 Cl H H 2-CH═CHMe, 6-OMe 0 0 982 Cl H H 2,6-(CH₂CH═CH₂)₂ 0 0983 Cl H H 2-CH₂CH═CH₂, 6-CN 0 0 984 Cl H H 2-CH₂CH═CH₂, 6-OMe 0 0 985Cl H H 2,6-(CN)₂ 0 0 986 Cl H H 2-CN, 6-OMe 0 0 987 Cl H H 2,6-(OMe)₂ 00 988 Cl H H 3,5-F₂ 0 0 989 Cl H H 3-F, 5-Cl 0 0 990 Cl H H 3-F, 5-Br 00 991 Cl H H 3-F, 5-I 0 0 992 Cl H H 3,5-Cl₂ 0 0 993 Cl H H 3-Cl, 5-Br 00 994 Cl H H 3-Cl, 5-I 0 0 995 Cl H H 3,5-Br₂ 0 0 996 Cl H H 3-Br, 5-I 00 997 Cl H H 3,5-I₂ 0 0 998 Cl H H 3,5-Me₂ 0 0 999 Cl H H 3-Me, 5-Et 0 01000 Cl H H 3-Me, 5-iPr 0 0 1001 Cl H H 3-Me, 5-cPr 0 0 1002 Cl H H3-Me, 5-cBu 0 0 1003 Cl H H 3-Me, 5-CF₃ 0 0 1004 Cl H H 3-Me, 5-CN 0 01005 Cl H H 3-Me, 5-NO₂ 0 0 1006 Cl H H 3-Me, 5-OMe 0 0 1007 Cl H H3,5-iPr₂ 0 0 1008 Cl H H 3-iPr, 5-CF₃ 0 0 1009 Cl H H 3,5-(CF₃)₂ 0 01010 Cl H H 2-F, 3,5-Me₂ 0 0 1011 Cl H H 2-Cl, 3,5-Me₂ 0 0 1012 Cl H H2,3,5-Cl₃ 0 0 1013 Cl H H 2-Br, 3,5-Me₂ 0 0 1014 Cl H H 2-Br, 3,5-Cl₂ 00 1015 Cl H H 2-I, 3,5-Me₂ 0 0 1016 Cl H H 2,3,5-Me₃ 0 0 1017 Cl H H2-Me, 3,5-Cl₂ 0 0 1018 Cl H H 2-Et, 3,5-Me₂ 0 0 1019 Cl H H 2-Et,3,5-Cl₂ 0 0 1020 Cl H H 2-Pr, 3,5-Me₂ 0 0 1021 Cl H H 2-iPr, 3,5-Me₂ 0 01022 Cl H H 2-iPr, 3,5-Cl₂ 0 0 1023 Cl H H 2-cPr, 3,5-Me₂ 0 0 1024 Cl HH 2-cBu, 3,5-Me₂ 0 0 1025 Cl H H 2-CN, 3,5-Me₂ 0 0 1026 Cl H H 2-OMe,3,5-Me₂ 0 0 1027 Cl H H 2-SMe, 3,5-Me₂ 0 0 1028 Cl H H 2-F, 3,6-Me₂ 0 01029 Cl H H 2-F, 3-Me, 6-cPr 0 0 1030 Cl H H 2-F, 3-Me, 6-OMe 0 0 1031Cl H H 2-Cl, 3,6-Me₂ 0 0 1032 Cl H H 2-Cl, 3-Me, 6-cPr 0 0 1033 Cl H H2-Cl, 3-Me, 6-OMe 0 0 1034 Cl H H 2,3,6-Cl₃ 0 0 1035 Cl H H 2,3-Cl₂,6-cPr 0 0 1036 Cl H H 2-Br, 3,6-Cl₂ 0 0 1037 Cl H H 2,6-Br₂, 3-Cl 0 01038 Cl H H 2-Br, 3-Cl, 6-cPr 0 0 1039 Cl H H 2,6-Br₂, 3-Me 0 0 1040 ClH H 2-Br, 3,6-Me₂ 0 0 1041 Cl H H 2-Br, 3-Me, 6-cPr 0 0 1042 Cl H H2-Br, 3-Me, 6-OMe 0 0 1043 Cl H H 2,2,3-CN 0 0 1044 Cl H H 2-Br, 3-CN,6-cPr 0 0 1045 Cl H H 2,6-Br₂, 3-OMe 0 0 1046 Cl H H 2-Br, 3-OMe, 6-cPr0 0 1047 Cl H H 2-I, 3,6-Me₂ 0 0 1048 Cl H H 2-Me, 3,6-F₂ 0 0 1049 Cl HH 2-Me, 3-F, 6-Cl 0 0 1050 Cl H H 2-Me, 3-F, 6-Br 0 0 1051 Cl H H 2-Me,3-F, 6-I 0 0 1052 Cl H H 2-Me, 3-F, 6-cPr 0 0 1053 Cl H H 2-Me, 3-Cl,6-Br 0 0 1054 Cl H H 2-Me, 3-Cl, 6-I 0 0 1055 Cl H H 2-Me, 3-Cl, 6-cPr 00 1056 Cl H H 2,3-Me₂, 6-F 0 0 1057 Cl H H 2,3-Me₂, 6-Cl 0 0 1058 Cl H H2,3-Me₂, 6-Br 0 0 1059 Cl H H 2,3-Me₂, 6-I 0 0 1060 Cl H H 2,3,6-Me₃ 0 01061 Cl H H 2,3-Me₂, 6-cPr 0 0 1062 Cl H H 2,3-Me₂, 6-CN 0 0 1063 Cl H H2,3-Me₂, 6-CH═NOMe 0 0 1064 Cl H H 2,3-Me₂, 6-OMe 0 0 1065 Cl H H 2-Me,3-OMe, 6-Cl 0 0 1066 Cl H H 2-Me, 3-OMe, 6-Br 0 0 1067 Cl H H 2-Me,3-OMe, 6-I 0 0 1068 Cl H H 2,6-Me₂, 3-OMe 0 0 1069 Cl H H 2-Me, 3-OMe,6-cPr 0 0 1070 Cl H H 2-cPr, 3-Me, 6-F 0 0 1071 Cl H H 2-cPr, 3-Me, 6-Cl0 0 1072 Cl H H 2-cPr, 3-Me, 6-Br 0 0 1073 Cl H H 2-cPr, 3,6-Me₂ 0 01074 Cl H H 2-cPr, 3-Me, 6-Et 0 0 1075 Cl H H 2,6-cPr₂, 3-Me 0 0 1076 ClH H 2-cPr, 3-Me, 6-CN 0 0 1077 Cl H H 2-cPr, 3-Me, 6-OMe 0 0 1078 Cl H H2-cBu, 3,6-Me₂ 0 0 1079 Cl H H 2-CH₂CH═CH₂, 3,6-Me₂ 0 0 1080 Cl H H2-CH₂CH═CH₂, 3-OMe, 6-Et 0 0 1081 Cl H H 2-CN, 3,6-Me₂ 0 0 1082 Cl H H2-OMe, 3,6-Me₂ 0 0 1083 Cl H H 2-CH₂SMe, 3,6-Me₂ 0 0 1084 Cl H H 6-F,2-CH₂CH₂CH₂-3 0 0 1085 Cl H H 6-Cl, 2-CH₂CH₂CH₂-3 0 0 1086 Cl H H 6-Br,2-CH₂CH₂CH₂-3 0 0 1087 Cl H H 6-I, 2-CH₂CH₂CH₂-3 0 0 1088 Cl H H 6-Me,2-CH₂CH₂CH₂-3 0 0 1089 Cl H H 6-Et, 2-CH₂CH₂CH₂-3 0 0 1090 Cl H H 6-iPr,2-CH₂CH₂CH₂-3 0 0 1091 Cl H H 6-cPr, 2-CH₂CH₂CH₂-3 0 0 1092 Cl H H 6-CN,2-CH₂CH₂CH₂-3 0 0 1093 Cl H H 6-OMe, 2-CH₂CH₂CH₂-3 0 0 1094 Cl H H 6-Cl,2-OCH₂CH₂-3 0 0 1095 Cl H H 6-Br, 2-OCH₂CH₂-3 0 0 1096 Cl H H 6-Me,2-OCH₂CH₂-3 0 0 1097 Cl H H 6-Et, 2-OCH₂CH₂-3 0 0 1098 Cl H H 6-cPr,2-OCH₂CH₂-3 0 0 1099 Cl H H 6-Br, 2-OCH═CH-3 0 0 1100 Cl H H 6-Me,2-OCH═CH-3 0 0 1101 Cl H H 6-Et, 2-OCH═CH-3 0 0 1102 Cl H H 6-cPr,2-OCH═CH-3 0 0 1103 Cl H H 6-Cl, 2-CH₂CH₂O-3 0 0 1104 Cl H H 6-Br,2-CH₂CH₂O-3 0 0 1105 Cl H H 6-Me, 2-CH₂CH₂O-3 0 0 1106 Cl H H 6-Et,2-CH₂CH₂O-3 0 0 1107 Cl H H 6-cPr, 2-CH₂CH₂O-3 0 0 1108 Cl H H 6-Br,2-CH═CHO-3 0 0 1109 Cl H H 6-Me, 2-CH═CHO-3 0 0 1110 Cl H H 6-Et,2-CH═CHO-3 0 0 1111 Cl H H 6-cPr, 2-CH═CHO-3 0 0 1112 Cl H H 2,4,6-F₃ 00 1113 Cl H H 2,4-F₂, 6-Me 0 0 1114 Cl H H 2,4-F₂, 6-cPr 0 0 1115 Cl H H2-F, 4,6-cPr₂ 0 0 1116 Cl H H 2,4,6-Cl₃ 0 0 1117 Cl H H 2,4,6-Br₃ 0 01118 Cl H H 2,4-Br₂, 3,6-Me₂ 0 0 1119 Cl H H 2-Br, 4,6-Me₂ 0 0 1120 Cl HH 2,4-I₂, 6-Et 0 0 1121 Cl H H 2-Me, 4-F, 6-cPr 0 0 1122 Cl H H2,4,6-Me₃ 0 0 1123 Cl H H 2,2,6-cPr 0 0 1124 Cl H H 2-Br, 3,5,6-Me₃ 0 01125 Cl H H 2,3,5,6-Me₄ 0 0 1126 Cl H H 2,3,3,6-cPr 0 0 1127 Cl H H2,3,5-Me₃, 6-CN 0 0 1128 Cl H H 2,3,3,6-OMe 0 0 1129 Cl H H 5,6-Me₂,2-CH₂CH₂CH₂-3 0 0 1130 Cl H H 5-Me, 6-cPr, 2-CH₂CH₂CH₂-3 0 0 1131 Cl H H5-Me, 6-CN, 2-CH₂CH₂CH₂-3 0 0 1132 Cl H H 5-Me, 6-OMe, 2-CH₂CH₂CH₂-3 0 01133 Cl H H 2-CH₂CH₂CH₂-3,5-CH₂CH₂CH₂-6 0 0 1134 Cl H COMe 2-F 0 0 1135Cl H COMe 2-Cl 0 0 1136 Cl H COMe 2-Br 0 0 1137 Cl H COMe 2-I 0 0 1138Cl H COMe 2-Me 0 0 1139 Cl H COMe 2-iPr 0 0 1140 Cl H COMe 2-cPr 0 01141 Cl H COMe 2-cBu 0 0 1142 Cl H COMe 2-CH₂CH₂CH₂-3 0 0 1143 Cl H COMe2-cPr, 5-Me 0 0 1144 Cl H COMe 2-OMe, 5-Me 0 0 1145 Cl H COMe 2-F, 6-iPr0 0 1146 Cl H COMe 2-Cl, 6-cPr 0 0 1147 Cl H COMe 2-Br, 6-Me 0 0 1148 ClH COMe 2-I, 6-Me 0 0 1149 Cl H COMe 2,6-Me₂ 0 0 1150 Cl H COMe 2-Me,6-Et 0 0 1151 Cl H COMe 2-Me, 6-cPr 0 0 1152 Cl H COMe 2,6-cPr₂ 0 0 1153Cl H COMe 2-cPr, 3,5-Me₂ 0 0 1154 Cl H COMe 2-cPr, 5,6-Me₂ 0 0 1155 Cl HCOEt 2-Me 0 0 1156 Cl H COEt 2-iPr 0 0 1157 Cl H COEt 2-cPr 0 0 1158 ClH COEt 2-CH₂CH₂CH₂-3 0 0 1159 Cl H COEt 2,6-Me₂ 0 0 1160 Cl H COEt 2-Me,6-cPr 0 0 1161 Cl H COPr 2-Me 0 0 1162 Cl H COPr 2-iPr 0 0 1163 Cl HCOPr 2-cPr 0 0 1164 Cl H COPr 2-CH₂CH₂CH₂-3 0 0 1165 Cl H COPr 2,6-Me₂ 00 1166 Cl H COPr 2-Me, 6-cPr 0 0 1167 Cl H COiPr 2-Me 0 0 1168 Cl HCOiPr 2-iPr 0 0 1169 Cl H COiPr 2-cPr 0 0 1170 Cl H COiPr 2-CH₂CH₂CH₂-30 0 1171 Cl H COiPr 2,6-Me₂ 0 0 1172 Cl H COiPr 2-Me, 6-cPr 0 0 1173 ClH COBu 2-Me 0 0 1174 Cl H COBu 2-iPr 0 0 1175 Cl H COBu 2-cPr 0 0 1176Cl H COBu 2-CH₂CH₂CH₂-3 0 0 1177 Cl H COBu 2,6-Me₂ 0 0 1178 Cl H COBu2-Me, 6-cPr 0 0 1179 Cl H COiBu 2-Me 0 0 1180 Cl H COiBu 2-iPr 0 0 1181Cl H COiBu 2-cPr 0 0 1182 Cl H COiBu 2-CH₂CH₂CH₂-3 0 0 1183 Cl H COiBu2,6-Me₂ 0 0 1184 Cl H COiBu 2-Me, 6-cPr 0 0 1185 Cl H COsBu 2-Me 0 01186 Cl H COsBu 2-iPr 0 0 1187 Cl H COsBu 2-cPr 0 0 1188 Cl H COsBu2-CH₂CH₂CH₂-3 0 0 1189 Cl H COsBu 2,6-Me₂ 0 0 1190 Cl H COsBu 2-Me,6-cPr 0 0 1191 Cl H COtBu 2-Cl 0 0 1192 Cl H COtBu 2-Br 0 0 1193 Cl HCOtBu 2-I 0 0 1194 Cl H COtBu 2-Me 0 0 1195 Cl H COtBu 2-iPr 0 0 1196 ClH COtBu 2-cPr 0 0 1197 Cl H COtBu 2-cBu 0 0 1198 Cl H COtBu2-CH₂CH₂CH₂-3 0 0 1199 Cl H COtBu 2-cPr, 5-Me 0 0 1200 Cl H COtBu 2-OMe,5-Me 0 0 1201 Cl H COtBu 2-F, 6-iPr 0 0 1202 Cl H COtBu 2-Cl, 6-cPr 0 01203 Cl H COtBu 2-Br, 6-Me 0 0 1204 Cl H COtBu 2-I, 6-Me 0 0 1205 Cl HCOtBu 2,6-Me₂ 0 0 1206 Cl H COtBu 2-Me, 6-Et 0 0 1207 Cl H COtBu 2-Me,6-cPr 0 0 1208 Cl H COtBu 2,6-cPr₂ 0 0 1209 Cl H COtBu 2-cPr, 3,5-Me₂ 00 1210 Cl H COtBu 2-cPr, 5,6-Me₂ 0 0 1211 Cl H COtPen 2-Me 0 0 1212 Cl HCOtPen 2-iPr 0 0 1213 Cl H COtPen 2-cPr 0 0 1214 Cl H COtPen2-CH₂CH₂CH₂-3 0 0 1215 Cl H COtPen 2,6-Me₂ 0 0 1216 Cl H COtPen 2-Me,6-cPr 0 0 1217 Cl H COHx 2-Me 0 0 1218 Cl H COHx 2-iPr 0 0 1219 Cl HCOHx 2-cPr 0 0 1220 Cl H COHx 2-CH₂CH₂CH₂-3 0 0 1221 Cl H COHx 2,6-Me₂ 00 1222 Cl H COHx 2-Me, 6-cPr 0 0 1223 Cl H COC₇H₁₅ 2-Me 0 0 1224 Cl HCOC₇H₁₅ 2-iPr 0 0 1225 Cl H COC₇H₁₅ 2-cPr 0 0 1226 Cl H COC₇H₁₅2-CH₂CH₂CH₂-3 0 0 1227 Cl H COC₇H₁₅ 2,6-Me₂ 0 0 1228 Cl H COC₇H₁₅ 2-Me,6-cPr 0 0 1229 Cl H COC₈H₁₇ 2-Me 0 0 1230 Cl H COC₈H₁₇ 2-iPr 0 0 1231 ClH COC₈H₁₇ 2-cPr 0 0 1232 Cl H COC₈H₁₇ 2-CH₂CH₂CH₂-3 0 0 1233 Cl HCOC₈H₁₇ 2,6-Me₂ 0 0 1234 Cl H COC₈H₁₇ 2-Me, 6-cPr 0 0 1235 Cl H COC₉H₁₉2-Cl 0 0 1236 Cl H COC₉H₁₉ 2-Br 0 0 1237 Cl H COC₉H₁₉ 2-I 0 0 1238 Cl HCOC₉H₁₉ 2-Me 0 0 1239 Cl H COC₉H₁₉ 2-iPr 0 0 1240 Cl H COC₉H₁₉ 2-cPr 0 01241 Cl H COC₉H₁₉ 2-cBu 0 0 1242 Cl H COC₉H₁₉ 2-CH₂CH₂CH₂-3 0 0 1243 ClH COC₉H₁₉ 2-cPr, 5-Me 0 0 1244 Cl H COC₉H₁₉ 2-OMe, 5-Me 0 0 1245 Cl HCOC₉H₁₉ 2-F, 6-iPr 0 0 1246 Cl H COC₉H₁₉ 2-Cl, 6-cPr 0 0 1247 Cl HCOC₉H₁₉ 2-Br, 6-Me 0 0 1248 Cl H COC₉H₁₉ 2-I, 6-Me 0 0 1249 Cl H COC₉H₁₉2,6-Me₂ 0 0 1250 Cl H COC₉H₁₉ 2-Me, 6-Et 0 0 1251 Cl H COC₉H₁₉ 2-Me,6-cPr 0 0 1252 Cl H COC₉H₁₉ 2,6-cPr₂ 0 0 1253 Cl H COC₉H₁₉ 2-cPr,3,5-Me₂ 0 0 1254 Cl H COC₉H₁₉ 2-cPr, 5,6-Me₂ 0 0 1255 Cl H COC₁₄H₂₉ 2-Me0 0 1256 Cl H COC₁₄H₂₉ 2-iPr 0 0 1257 Cl H COC₁₄H₂₉ 2-cPr 0 0 1258 Cl HCOC₁₄H₂₉ 2-CH₂CH₂CH₂-3 0 0 1259 Cl H COC₁₄H₂₉ 2,6-Me₂ 0 0 1260 Cl HCOC₁₄H₂₉ 2-Me, 6-cPr 0 0 1261 Cl H COcPr 2-Cl 0 0 1262 Cl H COcPr 2-Br 00 1263 Cl H COcPr 2-I 0 0 1264 Cl H COcPr 2-Me 0 0 1265 Cl H COcPr 2-iPr0 0 1266 Cl H COcPr 2-cPr 0 0 1267 Cl H COcPr 2-cBu 0 0 1268 Cl H COcPr2-CH₂CH₂CH₂-3 0 0 1269 Cl H COcPr 2-cPr, 5-Me 0 0 1270 Cl H COcPr 2-OMe,5-Me 0 0 1271 Cl H COcPr 2-F, 6-iPr 0 0 1272 Cl H COcPr 2-Cl, 6-cPr 0 01273 Cl H COcPr 2-Br, 6-Me 0 0 1274 Cl H COcPr 2-I, 6-Me 0 0 1275 Cl HCOcPr 2,6-Me₂ 0 0 1276 Cl H COcPr 2-Me, 6-Et 0 0 1277 Cl H COcPr 2-Me,6-cPr 0 0 1278 Cl H COcPr 2,6-cPr₂ 0 0 1279 Cl H COcPr 2-cPr, 3,5-Me₂ 00 1280 Cl H COcPr 2-cPr, 5,6-Me₂ 0 0 1281 Cl H COcBu 2-Me 0 0 1282 Cl HCOcBu 2-iPr 0 0 1283 Cl H COcBu 2-cPr 0 0 1284 Cl H COcBu 2-CH₂CH₂CH₂-30 0 1285 Cl H COcBu 2,6-Me₂ 0 0 1286 Cl H COcBu 2-Me, 6-cPr 0 0 1287 ClH COcPen 2-Me 0 0 1288 Cl H COcPen 2-iPr 0 0 1289 Cl H COcPen 2-cPr 0 01290 Cl H COcPen 2-CH₂CH₂CH₂-3 0 0 1291 Cl H COePen 2,6-Me₂ 0 0 1292 ClH COcPen 2-Me, 6-cPr 0 0 1293 Cl H COcHx 2-Me 0 0 1294 Cl H COcHx 2-iPr0 0 1295 Cl H COcHx 2-cPr 0 0 1296 Cl H COcHx 2-CH₂CH₂CH₂-3 0 0 1297 ClH COcHx 2,6-Me₂ 0 0 1298 Cl H COcHx 2-Me, 6-cPr 0 0 1299 Cl H COCF₃ 2-Me0 0 1300 Cl H COCF₃ 2-iPr 0 0 1301 Cl H COCF₃ 2-cPr 0 0 1302 Cl H COCF₃2-CH₂CH₂CH₂-3 0 0 1303 Cl H COCF₃ 2,6-Me₂ 0 0 1304 Cl H COCF₃ 2-Me,6-cPr 0 0 1305 Cl H COCH₂Cl 2-Me 0 0 1306 Cl H COCH₂Cl 2-iPr 0 0 1307 ClH COCH₂Cl 2-cPr 0 0 1308 Cl H COCH₂Cl 2-CH₂CH₂CH₂-3 0 0 1309 Cl HCOCH₂Cl 2,6-Me₂ 0 0 1310 Cl H COCH₂Cl 2-Me, 6-cPr 0 0 1311 Cl H COCCl₃2-Me 0 0 1312 Cl H COCCl₃ 2-iPr 0 0 1313 Cl H COCCl₃ 2-cPr 0 0 1314 Cl HCOCCl₃ 2-CH₂CH₂CH₂-3 0 0 1315 Cl H COCCl₃ 2,6-Me₂ 0 0 1316 Cl H COCCl₃2-Me, 6-cPr 0 0 1317 Cl H COCH₂Br 2-Me 0 0 1318 Cl H COCH₂Br 2-iPr 0 01319 Cl H COCH₂Br 2-cPr 0 0 1320 Cl H COCH₂Br 2-CH₂CH₂CH₂-3 0 0 1321 ClH COCH₂Br 2,6-Me₂ 0 0 1322 Cl H COCH₂Br 2-Me, 6-cPr 0 0 1323 Cl HCOCH₂CF₃ 2-Me 0 0 1324 Cl H COCH₂CF₃ 2-iPr 0 0 1325 Cl H COCH₂CF₃ 2-cPr0 0 1326 Cl H COCH₂CF₃ 2-CH₂CH₂CH₂-3 0 0 1327 Cl H COCH₂CF₃ 2,6-Me₂ 0 01328 Cl H COCH₂CF₃ 2-Me, 6-cPr 0 0 1329 Cl H COCHBrEt 2-Me 0 0 1330 Cl HCOCHBrEt 2-iPr 0 0 1331 Cl H COCHBrEt 2-cPr 0 0 1332 Cl H COCHBrEt2-CH₂CH₂CH₂-3 0 0 1333 Cl H COCHBrEt 2,6-Me₂ 0 0 1334 Cl H COCHBrEt2-Me, 6-cPr 0 0 1335 Cl H COCH₂CH₂CH₂Cl 2-Me 0 0 1336 Cl H COCH₂CH₂CH₂Cl2-iPr 0 0 1337 Cl H COCH₂CH₂CH₂Cl 2-cPr 0 0 1338 Cl H COCH₂CH₂CH₂Cl2-CH₂CH₂CH₂-3 0 0 1339 Cl H COCH₂CH₂CH₂Cl 2,6-Me₂ 0 0 1340 Cl HCOCH₂CH₂CH₂Cl 2-Me, 6-cPr 0 0 1341 Cl H COCH═CH₂ 2-Me 0 0 1342 Cl HCOCH═CH₂ 2-iPr 0 0 1343 Cl H COCH═CH₂ 2-cPr 0 0 1344 Cl H COCH═CH₂2-CH₂CH₂CH₂-3 0 0 1345 Cl H COCH═CH₂ 2,6-Me₂ 0 0 1346 Cl H COCH═CH₂2-Me, 6-cPr 0 0 1347 Cl H COCH═CHMe 2-Me 0 0 1348 Cl H COCH═CHMe 2-iPr 00 1349 Cl H COCH═CHMe 2-cPr 0 0 1350 Cl H COCH═CHMe 2-CH₂CH₂CH₂-3 0 01351 Cl H COCH═CHMe 2,6-Me₂ 0 0 1352 Cl H COCH═CHMe 2-Me, 6-cPr 0 0 1353Cl H COCH═CMe₂ 2-Me 0 0 1354 Cl H COCH═CMe₂ 2-iPr 0 0 1355 Cl HCOCH═CMe₂ 2-cPr 0 0 1356 Cl H COCH═CMe₂ 2-CH₂CH₂CH₂-3 0 0 1357 Cl HCOCH═CMe₂ 2,6-Me₂ 0 0 1358 Cl H COCH═CMe₂ 2-Me, 6-cPr 0 0 1359 Cl HCOCH═CHPh 2-Me 0 0 1360 Cl H COCH═CHPh 2-iPr 0 0 1361 Cl H COCH═CHPh2-cPr 0 0 1362 Cl H COCH═CHPh 2-CH₂CH₂CH₂-3 0 0 1363 Cl H COCH═CHPh2,6-Me₂ 0 0 1364 Cl H COCH═CHPh 2-Me, 6-cPr 0 0 1365 Cl H COC CH 2-Me 00 1366 Cl H COC CH 2-iPr 0 0 1367 Cl H COC CH 2-cPr 0 0 1368 Cl H COC CH2-CH₂CH₂CH₂-3 0 0 1369 Cl H COC CH 2,6-Me₂ 0 0 1370 Cl H COC CH 2-Me,6-cPr 0 0 1371 Cl H COCH₂Ph 2-Me 0 0 1372 Cl H COCH₂Ph 2-iPr 0 0 1373 ClH COCH₂Ph 2-cPr 0 0 1374 Cl H COCH₂Ph 2-CH₂CH₂CH₂-3 0 0 1375 Cl HCOCH₂Ph 2,6-Me₂ 0 0 1376 Cl H COCH₂Ph 2-Me, 6-cPr 0 0 1377 Cl HCOCH₂CH₂CO₂Me 2-Me 0 0 1378 Cl H COCH₂CH₂CO₂Me 2-iPr 0 0 1379 Cl HCOCH₂CH₂CO₂Me 2-cPr 0 0 1380 Cl H COCH₂CH₂CO₂Me 2-CH₂CH₂CH₂-3 0 0 1381Cl H COCH₂CH₂CO₂Me 2,6-Me₂ 0 0 1382 Cl H COCH₂CH₂CO₂Me 2-Me, 6-cPr 0 01383 Cl H COPh 2-F 0 0 1384 Cl H COPh 2-Cl 0 0 1385 Cl H COPh 2-Br 0 01386 Cl H COPh 2-I 0 0 1387 Cl H COPh 2-Me 0 0 1388 Cl H COPh 2-Et 0 01389 Cl H COPh 2-iPr 0 0 1390 Cl H COPh 2-tBu 0 0 1391 Cl H COPh 2-cPr 00 1392 Cl H COPh 2-(cPr-1-Me) 0 0 1393 Cl H COPh 2-(cPr-2-Me) 0 0 1394Cl H COPh 2-(cPr-2,2-Cl₂) 0 0 1395 Cl H COPh 2-cBu 0 0 1396 Cl H COPh4-SiMe₃ 0 0 1397 Cl H COPh 2-CH₂CH₂CH₂-3 0 0 1398 Cl H COPh 2-CH═CHO-3 00 1399 Cl H COPh 2-CH₂CH₂O-3 0 0 1400 Cl H COPh 2-OCH═CH-3 0 0 1401 Cl HCOPh 2-OCH₂CH₂-3 0 0 1402 Cl H COPh 2-cPr, 5-F 0 0 1403 Cl H COPh 2-cPr,5-Cl 0 0 1404 Cl H COPh 2-cPr, 5-Me 0 0 1405 Cl H COPh 2-OMe, 5-Me 0 01406 Cl H COPh 2-F, 6-iPr 0 0 1407 Cl H COPh 2-F, 6-cPr 0 0 1408 Cl HCOPh 2-Cl, 6-Me 0 0 1409 Cl H COPh 2-Cl, 6-cPr 0 0 1410 Cl H COPh 2-Br,6-Me 0 0 1411 Cl H COPh 2-Br, 6-Et 0 0 1412 Cl H COPh 2-Br, 6-cPr 0 01413 Cl H COPh 2-I, 6-Me 0 0 1414 Cl H COPh 2-I, 6-Et 0 0 1415 Cl H COPh2,6-Me₂ 0 0 1416 Cl H COPh 2-Me, 6-Et 0 0 1417 Cl H COPh 2-Me, 6-cPr 0 01418 Cl H COPh 2-Et, 6-cPr 0 0 1419 Cl H COPh 2-iPr, 6-cPr 0 0 1420 Cl HCOPh 2-tBu, 6-cPr 0 0 1421 Cl H COPh 2,6-cPr₂ 0 0 1422 Cl H COPh 2-cPr,6-OMe 0 0 1423 Cl H COPh 2-Br, 3,6-Me₂ 0 0 1424 Cl H COPh 2-cPr, 3,5-Me₂0 0 1425 Cl H COPh 2-cPr,4, 6-Me₂ 0 0 1426 Cl H COPh 2-Br, 5,6-Me₂ 0 01427 Cl H COPh 2-cPr, 5,6-Me₂ 0 0 1428 Cl H COPh 2-Br, 5-CH═CH—O-6 0 01429 Cl H COPh 2-Me, 5-CH₂CH₂CH₂-6 0 0 1430 Cl H COPh 2-Me, 5-CH₂CH₂O-60 0 1431 Cl H COPh 2-Me, 5-CH═CH—O-6 0 0 1432 Cl H COPh 2-Et,5-CH₂CH₂CH₂-6 0 0 1433 Cl H COPh 2-cPr, 5-CH₂CH₂CH₂-6 0 0 1434 Cl H COPh2-cPr, 5-CH═CH—O-6 0 0 1435 Cl H COPh 2-Br, 3,5,6-Me₃ 0 0 1436 Cl HCO(Ph-2-Cl) 2-Me 0 0 1437 Cl H CO(Ph-2-Cl) 2-iPr 0 0 1438 Cl HCO(Ph-2-Cl) 2-cPr 0 0 1439 Cl H CO(Ph-2-Cl) 2-CH₂CH₂CH₂-3 0 0 1440 Cl HCO(Ph-2-Cl) 2,6-Me₂ 0 0 1441 Cl H CO(Ph-2-Cl) 2-Me, 6-cPr 0 0 1442 Cl HCO(Ph-2-Me) 2-F 0 0 1443 Cl H CO(Ph-2-Me) 2-Cl 0 0 1444 Cl H CO(Ph-2-Me)2-Br 0 0 1445 Cl H CO(Ph-2-Me) 2-I 0 0 1446 Cl H CO(Ph-2-Me) 2-Me 0 01447 Cl H CO(Ph-2-Me) 2-Et 0 0 1448 Cl H CO(Ph-2-Me) 2-iPr 0 0 1449 Cl HCO(Ph-2-Me) 2-tBu 0 0 1450 Cl H CO(Ph-2-Me) 2-sBu 0 0 1451 Cl HCO(Ph-2-Me) 2-(cPr-1-Me) 0 0 1452 Cl H CO(Ph-2-Me) 2-cPr 0 0 1453 Cl HCO(Ph-2-Me) 2-(cPr-2,2-Cl₂) 0 0 1454 Cl H CO(Ph-2-Me) 2-cBu 0 0 1455 ClH CO(Ph-2-Me) 2-cHx 0 0 1456 Cl H CO(Ph-2-Me) 2-Ph 0 0 1457 Cl HCO(Ph-2-Me) 3-tBu 0 0 1458 Cl H CO(Ph-2-Me) 3-OMe 0 0 1459 Cl HCO(Ph-2-Me) 2-iPr, 5-Me 0 0 1460 Cl H CO(Ph-2-Me) 2-CH₂CH₂CH₂-3 0 0 1461Cl H CO(Ph-2-Me) 2-CH═CH═CH═CH-3 0 0 1462 Cl H CO(Ph-2-Me) 2-CH═CHO-3 00 1463 Cl H CO(Ph-2-Me) 2-CH₂CH₂O-3 0 0 1464 Cl H CO(Ph-2-Me) 2-OCH═CH-30 0 1465 Cl H CO(Ph-2-Me) 2-OCH₂CH₂-3 0 0 1466 Cl H CO(Ph-2-Me) 2-cPr,5-F 0 0 1467 Cl H CO(Ph-2-Me) 2-cPr, 5-Cl 0 0 1468 Cl H CO(Ph-2-Me)2-cPr, 5-Me 0 0 1469 Cl H CO(Ph-2-Me) 2-OMe, 5-Me 0 0 1470 Cl HCO(Ph-2-Me) 2-F, 6-iPr 0 0 1471 Cl H CO(Ph-2-Me) 2-F, 6-cPr 0 0 1472 ClH CO(Ph-2-Me) 2-Cl, 6-Me 0 0 1473 Cl H CO(Ph-2-Me) 2-Cl, 6-cPr 0 0 1474Cl H CO(Ph-2-Me) 2-Br, 6-Me 0 0 1475 Cl H CO(Ph-2-Me) 2-Br, 6-Et 0 01476 Cl H CO(Ph-2-Me) 2-Br, 6-cPr 0 0 1477 Cl H CO(Ph-2-Me) 2-I, 6-Me 00 1478 Cl H CO(Ph-2-Me) 2-I, 6-Et 0 0 1479 Cl H CO(Ph-2-Me) 2,6-Me₂ 0 01480 Cl H CO(Ph-2-Me) 2-Me, 6-Et 0 0 1481 Cl H CO(Ph-2-Me) 2-Me, 6-cPr 00 1482 Cl H CO(Ph-2-Me) 2-Et, 6-cPr 0 0 1483 Cl H CO(Ph-2-Me) 2-iPr,6-cPr 0 0 1484 Cl H CO(Ph-2-Me) 2-tBu, 6-cPr 0 0 1485 Cl H CO(Ph-2-Me)2,6-cPr₂ 0 0 1486 Cl H CO(Ph-2-Me) 2-cPr, 6-OMe 0 0 1487 Cl HCO(Ph-2-Me) 2-Br, 3,6-Me₂ 0 0 1488 Cl H CO(Ph-2-Me) 2-cPr, 3,5-Me₂ 0 01489 Cl H CO(Ph-2-Me) 2-cPr, 4, 6-Me₂ 0 0 1490 Cl H CO(Ph-2-Me) 2-Br,5,6-Me₂ 0 0 1491 Cl H CO(Ph-2-Me) 2-cPr, 5,6-Me₂ 0 0 1492 Cl HCO(Ph-2-Me) 2-Br, 5-CH═CH-O-6 0 0 1493 Cl H CO(Ph-2-Me) 2-Me,5-CH₂CH₂CH₂-6 0 0 1494 Cl H CO(Ph-2-Me) 2-Me, 5-CH₂CH₂O-6 0 0 1495 Cl HCO(Ph-2-Me) 2-Me, 5-CH═CH—O-6 0 0 1496 Cl H CO(Ph-2-Me) 2-Et,5-CH₂CH₂CH₂-6 0 0 1497 Cl H CO(Ph-2-Me) 2-cPr, 5-CH₂CH₂CH₂-6 0 0 1498 ClH CO(Ph-2-Me) 2-cPr, 5-CH═CH—O-6 0 0 1499 Cl H CO(Ph-2-Me) 2-Br,3,5,6-Me₃ 0 0 1500 Cl H CO(Ph-2-CN) 2-Me 0 0 1501 Cl H CO(Ph-2-CN) 2-iPr0 0 1502 Cl H CO(Ph-2-CN) 2-cPr 0 0 1503 Cl H CO(Ph-2-CN) 2-CH₂CH₂CH₂-30 0 1504 Cl H CO(Ph-2-CN) 2,6-Me₂ 0 0 1505 Cl H CO(Ph-2-CN) 2-Me, 6-cPr0 0 1506 Cl H CO(Ph-2-OMe) 2-Cl 0 0 1507 Cl H CO(Ph-2-OMe) 2-Br 0 0 1508Cl H CO(Ph-2-OMe) 2-I 0 0 1509 Cl H CO(Ph-2-OMe) 2-Me 0 0 1510 Cl HCO(Ph-2-OMe) 2-iPr 0 0 1511 Cl H CO(Ph-2-OMe) 2-cPr 0 0 1512 Cl HCO(Ph-2-OMe) 2-cBu 0 0 1513 Cl H CO(Ph-2-OMe) 2-CH₂CH₂CH₂-3 0 0 1514 ClH CO(Ph-2-OMe) 2-cPr, 5-Me 0 0 1515 Cl H CO(Ph-2-OMe) 2-OMe, 5-Me 0 01516 Cl H CO(Ph-2-OMe) 2-F, 6-iPr 0 0 1517 Cl H CO(Ph-2-OMe) 2-Cl, 6-cPr0 0 1518 Cl H CO(Ph-2-OMe) 2-Br, 6-Me 0 0 1519 Cl H CO(Ph-2-OMe) 2-I,6-Me 0 0 1520 Cl H CO(Ph-2-OMe) 2,6-Me₂ 0 0 1521 Cl H CO(Ph-2-OMe) 2-Me,6-Et 0 0 1522 Cl H CO(Ph-2-OMe) 2-Me, 6-cPr 0 0 1523 Cl H CO(Ph-2-OMe)2,6-cPr₂ 0 0 1524 Cl H CO(Ph-2-OMe) 2-cPr, 3,5-Me₂ 0 0 1525 Cl HCO(Ph-2-OMe) 2-cPr, 5,6-Me₂ 0 0 1526 Cl H CO(Ph-3-Me) 2-Me 0 0 1527 Cl HCO(Ph-3-Me) 2-iPr 0 0 1528 Cl H CO(Ph-3-Me) 2-cPr 0 0 1529 Cl HCO(Ph-3-Me) 2-CH₂CH₂CH₂-3 0 0 1530 Cl H CO(Ph-3-Me) 2,6-Me₂ 0 0 1531 ClH CO(Ph-3-Me) 2-Me, 6-cPr 0 0 1532 Cl H CO(Ph-4-Cl) 2-Me 0 0 1533 Cl HCO(Ph-4-Cl) 2-iPr 0 0 1534 Cl H CO(Ph-4-Cl) 2-cPr 0 0 1535 Cl HCO(Ph-4-Cl) 2-CH₂CH₂CH₂-3 0 0 1536 Cl H CO(Ph-4-Cl) 2,6-Me₂ 0 0 1537 ClH CO(Ph-4-Cl) 2-Me, 6-cPr 0 0 1538 Cl H CO(Ph-4-Br) 2-Me 0 0 1539 Cl HCO(Ph-4-Br) 2-iPr 0 0 1540 Cl H CO(Ph-4-Br) 2-cPr 0 0 1541 Cl HCO(Ph-4-Br) 2-CH₂CH₂CH₂-3 0 0 1542 Cl H CO(Ph-4-Br) 2,6-Me₂ 0 0 1543 ClH CO(Ph-4-Br) 2-Me, 6-cPr 0 0 1544 Cl H CO(Ph-4-I) 2-Me 0 0 1545 Cl HCO(Ph-4-I) 2-iPr 0 0 1546 Cl H CO(Ph-4-I) 2-cPr 0 0 1547 Cl H CO(Ph-4-I)2-CH₂CH₂CH₂-3 0 0 1548 Cl H CO(Ph-4-I) 2,6-Me₂ 0 0 1549 Cl H CO(Ph-4-I)2-Me, 6-cPr 0 0 1550 Cl H CO(Ph-4-Me) 2-Cl 0 0 1551 Cl H CO(Ph-4-Me)2-Br 0 0 1552 Cl H CO(Ph-4-Me) 2-I 0 0 1553 Cl H CO(Ph-4-Me) 2-Me 0 01554 Cl H CO(Ph-4-Me) 2-iPr 0 0 1555 Cl H CO(Ph-4-Me) 2-cPr 0 0 1556 ClH CO(Ph-4-Me) 2-cBu 0 0 1557 Cl H CO(Ph-4-Me) 2-CH₂CH₂CH₂-3 0 0 1558 ClH CO(Ph-4-Me) 2-cPr, 5-Me 0 0 1559 Cl H CO(Ph-4-Me) 2-OMe, 5-Me 0 0 1560Cl H CO(Ph-4-Me) 2-F, 6-iPr 0 0 1561 Cl H CO(Ph-4-Me) 2-Cl, 6-cPr 0 01562 Cl H CO(Ph-4-Me) 2-Br, 6-Me 0 0 1563 Cl H CO(Ph-4-Me) 2-I, 6-Me 0 01564 Cl H CO(Ph-4-Me) 2,6-Me₂ 0 0 1565 Cl H CO(Ph-4-Me) 2-Me, 6-Et 0 01566 Cl H CO(Ph-4-Me) 2-Me, 6-cPr 0 0 1567 Cl H CO(Ph-4-Me) 2-cPr₂ 0 01568 Cl H CO(Ph-4-Me) 2-cPr, 3,5-Me₂ 0 0 1569 Cl H CO(Ph-4-Me) 2-cPr,5,6-Me₂ 0 0 1570 Cl H CO(Ph-4-tBu) 2-Me 0 0 1571 Cl H CO(Ph-4-tBu) 2-iPr0 0 1572 Cl H CO(Ph-4-tBu) 2-cPr 0 0 1573 Cl H CO(Ph-4-tBu)2-CH₂CH₂CH₂-3 0 0 1574 Cl H CO(Ph-4-tBu) 2,6-Me₂ 0 0 1575 Cl HCO(Ph-4-tBu) 2-Me, 6-cPr 0 0 1576 Cl H CO(Ph-4-CO₂Me) 2-Me 0 0 1577 Cl HCO(Ph-4-CO₂Me) 2-iPr 0 0 1578 Cl H CO(Ph-4-CO₂Me) 2-cPr 0 0 1579 Cl HCO(Ph-4-CO₂Me) 2-CH₂CH₂CH₂-3 0 0 1580 Cl H CO(Ph-4-CO₂Me) 2,6-Me₂ 0 01581 Cl H CO(Ph-4-CO₂Me) 2-Me, 6-cPr 0 0 1582 Cl H CO(Ph-4-COtBu) 2-Me 00 1583 Cl H CO(Ph-4-COtBu) 2-iPr 0 0 1584 Cl H CO(Ph-4-COtBu) 2-cPr 0 01585 Cl H CO(Ph-4-COtBu) 2-CH₂CH₂CH₂-3 0 0 1586 Cl H CO(Ph-4-COtBu)2,6-Me₂ 0 0 1587 Cl H CO(Ph-4-COtBu) 2-Me, 6-cPr 0 0 1588 Cl HCO(Ph-4-NO₂) 2-Me 0 0 1589 Cl H CO(Ph-4-NO₂) 2-iPr 0 0 1590 Cl HCO(Ph-4-NO₂) 2-cPr 0 0 1591 Cl H CO(Ph-4-NO₂) 2-CH₂CH₂CH₂-3 0 0 1592 ClH CO(Ph-4-NO₂) 2,6-Me₂ 0 0 1593 Cl H CO(Ph-4-NO₂) 2-Me, 6-cPr 0 0 1594Cl H CO(Ph-4-OMe) 2-Me 0 0 1595 Cl H CO(Ph-4-OMe) 2-iPr 0 0 1596 Cl HCO(Ph-4-OMe) 2-cPr 0 0 1597 Cl H CO(Ph-4-OMe) 2-CH₂CH₂CH₂-3 0 0 1598 ClH CO(Ph-4-OMe) 2,6-Me₂ 0 0 1599 Cl H CO(Ph-4-OMe) 2-Me, 6-cPr 0 0 1600Cl H CO(Ph-2,4-Cl₂) 2-Cl 0 0 1601 Cl H CO(Ph-2,4-Cl₂) 2-Br 0 0 1602 Cl HCO(Ph-2,4-Cl₂) 2-I 0 0 1603 Cl H CO(Ph-2, 4-Cl₂) 2-Me 0 0 1604 Cl HCO(Ph-2,4-Cl₂) 2-iPr 0 0 1605 Cl H CO(Ph-2,4-Cl₂) 2-cPr 0 0 1606 Cl HCO(Ph-2,4-Cl₂) 2-cBu 0 0 1607 Cl H CO(Ph-2,4-Cl₂) 2-CH₂CH₂CH₂-3 0 0 1608Cl H CO(Ph-2,4-Cl₂) 2-cPr, 5-Me 0 0 1609 Cl H CO(Ph-2,4-Cl₂) 2-OMe, 5-Me0 0 1610 Cl H CO(Ph-2,4-Cl₂) 2-F, 6-iPr 0 0 1611 Cl H CO(Ph-2,4-Cl₂)2-Cl, 6-cPr 0 0 1612 Cl H CO(Ph-2,4-Cl₂) 2-Br, 6-Me 0 0 1613 Cl HCO(Ph-2,4-Cl₂) 2-I, 6-Me 0 0 1614 Cl H CO(Ph-2,4-Cl₂) 2,6-Me₂ 0 0 1615Cl H CO(Ph-2,4-Cl₂) 2-Me, 6-Et 0 0 1616 Cl H CO(Ph-2,4-Cl₂) 2-Me, 6-cPr0 0 1617 Cl H CO(Ph-2,4-Cl₂) 2,6-cPr₂ 0 0 1618 Cl H CO(Ph-2,4-Cl₂)2-cPr, 3,5-Me₂ 0 0 1619 Cl H CO(Ph-2,4-Cl₂) 2-cPr, 5,6-Me₂ 0 0 1620 Cl HCO(Ph-2-CO₂Q⁵) 2-Me 0 0 1621 Cl H CO(Ph-2-CO₂Q⁵) 2-iPr 0 0 1622 Cl HCO(Ph-2-CO₂Q⁵) 2-cPr 0 0 1623 Cl H CO(Ph-2-CO₂Q⁵) 2-CH₂CH₂CH₂-3 0 0 1624Cl H CO(Ph-2-CO₂Q⁵) 2,6-Me₂ 0 0 1625 Cl H CO(Ph-2-CO₂Q⁵) 2-Me, 6-cPr 0 01626 Cl H CO(Ph-3-CO₂Q⁵) 2-Me 0 0 1627 Cl H CO(Ph-3-CO₂Q⁵) 2-iPr 0 01628 Cl H CO(Ph-3-CO₂Q⁵) 2-cPr 0 0 1629 Cl H CO(Ph-3-CO₂Q⁵)2-CH₂CH₂CH₂-3 0 0 1630 Cl H CO(Ph-3-CO₂Q⁵) 2,6-Me₂ 0 0 1631 Cl HCO(Ph-3-CO₂Q⁵) 2-Me, 6-cPr 0 0 1632 Cl H CO(Ph-4-CO₂Q⁵) 2-Me 0 0 1633 ClH CO(Ph-4-CO₂Q⁵) 2-iPr 0 0 1634 Cl H CO(Ph-4-CO₂Q⁵) 2-cPr 0 0 1635 Cl HCO(Ph-4-CO₂Q⁵) 2-CH₂CH₂CH₂-3 0 0 1636 Cl H CO(Ph-4-CO₂Q⁵) 2,6-Me₂ 0 01637 Cl H CO(Ph-4-CO₂Q⁵) 2-Me, 6-cPr 0 0 1638 Cl H CO(2-Fur) 2-Me 0 01639 Cl H CO(2-Fur) 2-iPr 0 0 1640 Cl H CO(2-Fur) 2-cPr 0 0 1641 Cl HCO(2-Fur) 2-CH₂CH₂CH₂-3 0 0 1642 Cl H CO(2-Fur) 2,6-Me₂ 0 0 1643 Cl HCO(2-Fur) 2-Me, 6-cPr 0 0 1644 Cl H CO(2-Thi) 2-Me 0 0 1645 Cl HCO(2-Thi) 2-iPr 0 0 1646 Cl H CO(2-Thi) 2-cPr 0 0 1647 Cl H CO(2-Thi)2-CH₂CH₂CH₂-3 0 0 1648 Cl H CO(2-Thi) 2,6-Me₂ 0 0 1649 Cl H CO(2-Thi)2-Me, 6-cPr 0 0 1650 Cl H CO₂Me 2-F 0 0 1651 Cl H CO₂Me 2-Cl 0 0 1652 ClH CO₂Me 2-Br 0 0 1653 Cl H CO₂Me 2-I 0 0 1654 Cl H CO₂Me 2-Me 0 0 1655Cl H CO₂Me 2-Et 0 0 1656 Cl H CO₂Me 2-iPr 0 0 1657 Cl H CO₂Me 2-tBu 0 01658 Cl H CO₂Me 2-cPr 0 0 1659 Cl H CO₂Me 2-(cPr-1-Me) 0 0 1660 Cl HCO₂Me 2-(cPr-2-Me) 0 0 1661 Cl H CO₂Me 2-(cPr-2,2-Cl₂) 0 0 1662 Cl HCO₂Me 2-cBu 0 0 1663 Cl H CO₂Me 2-CH₂CH₂CH₂-3 0 0 1664 Cl H CO₂Me2-CH═CH—O-3 0 0 1665 Cl H CO₂Me 2-CH₂CH₂O-3 0 0 1666 Cl H CO₂Me2-OCH═CH-3 0 0 1667 Cl H CO₂Me 2-OCH₂CH₂3 0 0 1668 Cl H CO₂Me 2-cPr, 5-F0 0 1669 Cl H CO₂Me 2-cPr, 5-Cl 0 0 1670 Cl H CO₂Me 2-cPr, 5-Me 0 0 1671Cl H CO₂Me 2-OMe, 5-Me 0 0 1672 Cl H CO₂Me 2-F, 6-iPr 0 0 1673 Cl HCO₂Me 2-F, 6-cPr 0 0 1674 Cl H CO₂Me 2-Cl, 6-Me 0 0 1675 Cl H CO₂Me2-Cl, 6-cPr 0 0 1676 Cl H CO₂Me 2-Br, 6-Me 0 0 1677 Cl H CO₂Me 2-Br,6-Et 0 0 1678 Cl H CO₂Me 2-Br, 6-cPr 0 0 1679 Cl H CO₂Me 2-I, 6-Me 0 01680 Cl H CO₂Me 2-I, 6-Et 0 0 1681 Cl H CO₂Me 2,6-Me₂ 0 0 1682 Cl HCO₂Me 2-Me, 6-Et 0 0 1683 Cl H CO₂Me 2-Me, 6-cPr 0 0 1684 Cl H CO₂Me2-Et, 6-cPr 0 0 1685 Cl H CO₂Me 2-iPr, 6-cPr 0 0 1686 Cl H CO₂Me 2-tBu,6-cPr 0 0 1687 Cl H CO₂Me 2,6-cPr₂ 0 0 1688 Cl H CO₂Me 2-cPr, 6-OMe 0 01689 Cl H CO₂Me 2-Br, 3,6-Me₂ 0 0 1690 Cl H CO₂Me 2-cPr, 3,2 0 0 1691 ClH CO₂Me 2-cPr, 4,6-Me₂ 0 0 1692 Cl H CO₂Me 2-Br, 5,6-Me₂ 0 0 1693 Cl HCO₂Me 2-cPr, 5,6-Me₂ 0 0 1694 Cl H CO₂Me 2-Br, 5-CH═CH—O-6 0 0 1695 Cl HCO₂Me 2-Me, 5-CH₂CH₂CH₂-6 0 0 1696 Cl H CO₂Me 2-Me, 5-CH₂CH₂O-6 0 0 1697Cl H CO₂Me 2-Me, 5-CH═CH—O-6 0 0 1698 Cl H CO₂Me 2-Et, 5-CH₂CH₂CH₂-6 0 01699 Cl H CO₂Me 2-cPr, 5-CH₂CH₂CH₂-6 0 0 1700 Cl H CO₂Me 2-cPr,5-CH═CH—O-6 0 0 1701 Cl H CO₂Me 2-Br, 3,5,6-Me₃ 0 0 1702 Cl H CO₂Et 2-F0 0 1703 Cl H CO₂Et 2-Cl 0 0 1704 Cl H CO₂Et 2-Br 0 0 1705 Cl H CO₂Et2-I 0 0 1706 Cl H CO₂Et 2-Me 0 0 1707 Cl H CO₂Et 2-Et 0 0 1708 Cl HCO₂Et 2-iPr 0 0 1709 Cl H CO₂Et 2-tBu 0 0 1710 Cl H CO₂Et 2-cPr 0 0 1711Cl H CO₂Et 2-(cPr-1-Me) 0 0 1712 Cl H CO₂Et 2-(cPr-2-Me) 0 0 1713 Cl HCO₂Et 2-(cPr-2,2-Cl₂) 0 0 1714 Cl H CO₂Et 2-cBu 0 0 1715 Cl H CO₂Et2-CH₂CH₂CH₂-3 0 0 1716 Cl H CO₂Et 2-CH═CH—O-3 0 0 1717 Cl H CO₂Et2-CH₂CH₂O-3 0 0 1718 Cl H CO₂Et 2-OCH═CH-3 0 0 1719 Cl H CO₂Et2-OCH₂CH₂-3 0 0 1720 Cl H CO₂Et 2-cPr, 5-F 0 0 1721 Cl H CO₂Et 2-cPr,5-Cl 0 0 1722 Cl H CO₂Et 2-cPr, 5-Me 0 0 1723 Cl H CO₂Et 2-OMe, 5-Me 0 01724 Cl H CO₂Et 2-F, 6-iPr 0 0 1725 Cl H CO₂Et 2-F, 6-cPr 0 0 1726 Cl HCO₂Et 2-Cl, 6-Me 0 0 1727 Cl H CO₂Et 2-Cl, 6-cPr 0 0 1728 Cl H CO₂Et2-Br, 6-Me 0 0 1729 Cl H CO₂Et 2-Br, 6-Et 0 0 1730 Cl H CO₂Et 2-Br,6-cPr 0 0 1731 Cl H CO₂Et 2-I, 6-Me 0 0 1732 Cl H CO₂Et 2-I, 6-Et 0 01733 Cl H CO₂Et 2,6-Me₂ 0 0 1734 Cl H CO₂Et 2-Me, 6-Et 0 0 1735 Cl HCO₂Et 2-Me, 6-cPr 0 0 1736 Cl H CO₂Et 2-Et, 6-cPr 0 0 1737 Cl H CO₂Et2-iPr, 6-cPr 0 0 1738 Cl H CO₂Et 2-tBu, 6-cPr 0 0 1739 Cl H CO₂Et2,6-cPr₂ 0 0 1740 Cl H CO₂Et 2-cPr, 6-OMe 0 0 1741 Cl H CO₂Et 2-Br,3,6-Me₂ 0 0 1742 Cl H CO₂Et 2-cPr, 3,5-Me₂ 0 0 1743 Cl H CO₂Et 2-cPr,4,6-Me₂ 0 0 1744 Cl H CO₂Et 2-Br, 5,6-Me₂ 0 0 1745 Cl H CO₂Et 2-cPr,5,6-Me₂ 0 0 1746 Cl H CO₂Et 2-Br, 5-CH═CH—O-6 0 0 1747 Cl H CO₂Et 2-Me,5-CH₂CH₂CH₂-6 0 0 1748 Cl H CO₂Et 2-Me, 5-CH₂CH₂O-6 0 0 1749 Cl H CO₂Et2-Me, 5-CH═CH—O-6 0 0 1750 Cl H CO₂Et 2-Et, 5-CH₂CH₂CH₂-6 0 0 1751 Cl HCO₂Et 2-cPr, 5-CH₂CH₂CH₂-6 0 0 1752 Cl H CO₂Et 2-cPr, 5-CH═CH—O-6 0 01753 Cl H CO₂Et 2-Br, 3,5,6-Me₃ 0 0 1754 Cl H CO₂iBu 2-Cl 0 0 1755 Cl HCO₂iBu 2-Br 0 0 1756 Cl H CO₂iBu 2-I 0 0 1757 Cl H CO₂iBu 2-Me 0 0 1758Cl H CO₂iBu 2-iPr 0 0 1759 Cl H CO₂iBu 2-cPr 0 0 1760 Cl H CO₂iBu 2-cBu0 0 1761 Cl H CO₂iBu 2-CH₂CH₂CH₂-3 0 0 1762 Cl H CO₂iBu 2-cPr, 5-Me 0 01763 Cl H CO₂iBu 2-OMe, 5-Me 0 0 1764 Cl H CO₂iBu 2-F, 6-iPr 0 0 1765 ClH CO₂iBu 2-Cl, 6-cPr 0 0 1766 Cl H CO₂iBu 2-Br, 6-Me 0 0 1767 Cl HCO₂iBu 2-I, 6-Me 0 0 1768 Cl H CO₂iBu 2,6-Me₂ 0 0 1769 Cl H CO₂iBu 2-Me,6-Et 0 0 1770 Cl H CO₂iBu 2-Me, 6-cPr 0 0 1771 Cl H CO₂iBu 2,6-cPr₂ 0 01772 Cl H CO₂iBu 2-cPr, 3,5-Me₂ 0 0 1773 Cl H CO₂iBu 2-cPr, 5,6-Me₂ 0 01774 Cl H CO₂Bu 2-Me 0 0 1775 Cl H CO₂Bu 2-iPr 0 0 1776 Cl H CO₂Bu 2-cPr0 0 1777 Cl H CO₂Bu 2-CH₂CH₂CH₂-3 0 0 1778 Cl H CO₂Bu 2,6-Me₂ 0 0 1779Cl H CO₂Bu 2-Me, 6-cPr 0 0 1780 Cl H CO₂CH₂Cl 2-Me 0 0 1781 Cl HCO₂CH₂Cl 2-iPr 0 0 1782 Cl H CO₂CH₂Cl 2-cPr 0 0 1783 Cl H CO₂CH₂Cl2-CH₂CH₂CH₂-3 0 0 1784 Cl H CO₂CH₂Cl 2,6-Me₂ 0 0 1785 Cl H CO₂CH₂Cl2-Me, 6-cPr 0 0 1786 Cl H CO₂CH₂CCl₃ 2-Cl 0 0 1787 Cl H CO₂CH₂CCl₃ 2-Br0 0 1788 Cl H CO₂CH₂CCl₃ 2-I 0 0 1789 Cl H CO₂CH₂CCl₃ 2-Me 0 0 1790 Cl HCO₂CH₂CCl₃ 2-iPr 0 0 1791 Cl H CO₂CH₂CCl₃ 2-cPr 0 0 1792 Cl H CO₂CH₂CCl₃2-cBu 0 0 1793 Cl H CO₂CH₂CCl₃ 2-CH₂CH₂CH₂-3 0 0 1794 Cl H CO₂CH₂CCl₃2-cPr, 5-Me 0 0 1795 Cl H CO₂CH₂CCl₃ 2-OMe, 5-Me 0 0 1796 Cl HCO₂CH₂CCl₃ 2-F, 6-iPr 0 0 1797 Cl H CO₂CH₂CCl₃ 2-Cl, 6-cPr 0 0 1798 Cl HCO₂CH₂CCl₃ 2-Br, 6-Me 0 0 1799 Cl H CO₂CH₂CCl₃ 2-I, 6-Me 0 0 1800 Cl HCO₂CH₂CCl₃ 2,6-Me₂ 0 0 1801 Cl H CO₂CH₂CCl₃ 2-Me, 6-Et 0 0 1802 Cl HCO₂CH₂CCl₃ 2-Me, 6-cPr 0 0 1803 Cl H CO₂CH₂CCl₃ 2,6-cPr₂ 0 0 1804 Cl HCO₂CH₂CCl₃ 2-cPr, 3,5-Me₂ 0 0 1805 Cl H CO₂CH₂CCl₃ 2-cPr, 5,6-Me₂ 0 01806 Cl H CO₂CH₂CH═CH₂ 2-Me 0 0 1807 Cl H CO₂CH₂CH═CH₂ 2-iPr 0 0 1808 ClH CO₂CH₂CH═CH₂ 2-cPr 0 0 1809 Cl H CO₂CH₂CH═CH₂ 2-CH₂CH₂CH₂-3 0 0 1810Cl H CO₂CH₂CH═CH₂ 2,6-Me₂ 0 0 1811 Cl H CO₂CH₂CH═CH₂ 2-Me, 6-cPr 0 01812 Cl H CO₂CH₂Ph 2-Me 0 0 1813 Cl H CO₂CH₂Ph 2-iPr 0 0 1814 Cl HCO₂CH₂Ph 2-cPr 0 0 1815 Cl H CO₂CH₂Ph 2-CH₂CH₂CH₂-3 0 0 1816 Cl HCO₂CH₂Ph 2,6-Me₂ 0 0 1817 Cl H CO₂CH₂Ph 2-Me, 6-cPr 0 0 1818 Cl HCO₂CH₂CH₂OMe 2-Me 0 0 1819 Cl H CO₂CH₂CH₂OMe 2-iPr 0 0 1820 Cl HCO₂CH₂CH₂OMe 2-cPr 0 0 1821 Cl H CO₂CH₂CH₂OMe 2-CH₂CH₂CH₂-3 0 0 1822 ClH CO₂CH₂CH₂OMe 2,6-Me₂ 0 0 1823 Cl H CO₂CH₂CH₂OMe 2-Me, 6-cPr 0 0 1824Cl H CO₂Ph 2-Cl 0 0 1825 Cl H CO₂Ph 2-Br 0 0 1826 Cl H CO₂Ph 2-I 0 01827 Cl H CO₂Ph 2-Me 0 0 1828 Cl H CO₂Ph 2-iPr 0 0 1829 Cl H CO₂Ph 2-cPr0 0 1830 Cl H CO₂Ph 2-cBu 0 0 1831 Cl H CO₂Ph 2-CH₂CH₂CH₂-3 0 0 1832 ClH CO₂Ph 2-cPr, 5-Me 0 0 1833 Cl H CO₂Ph 2-OMe, 5-Me 0 0 1834 Cl H CO₂Ph2-F, 6-iPr 0 0 1835 Cl H CO₂Ph 2-Cl, 6-cPr 0 0 1836 Cl H CO₂Ph 2-Br,6-Me 0 0 1837 Cl H CO₂Ph 2-I, 6-Me 0 0 1838 Cl H CO₂Ph 2,6-Me₂ 0 0 1839Cl H CO₂Ph 2-Me, 6-Et 0 0 1840 Cl H CO₂Ph 2-Me, 6-cPr 0 0 1841 Cl HCO₂Ph 2,6-cPr₂ 0 0 1842 Cl H CO₂Ph 2-cPr, 3,5-Me₂ 0 0 1843 Cl H CO₂Ph2-cPr, 5,6-Me₂ 0 0 1844 Cl H CO₂(Ph-4-Cl) 2-Me 0 0 1845 Cl HCO₂(Ph-4-Cl) 2-iPr 0 0 1846 Cl H CO₂(Ph-4-Cl) 2-cPr 0 0 1847 Cl HCO₂(Ph-4-Cl) 2-CH₂CH₂CH₂-3 0 0 1848 Cl H CO₂(Ph-4-Cl) 2,6-Me₂ 0 0 1849Cl H CO₂(Ph-4-Cl) 2-Me, 6-cPr 0 0 1850 Cl H CO₂ (Ph-4-NO₂) 2-Me 0 0 1851Cl H CO₂ (Ph-4-NO₂) 2-iPr 0 0 1852 Cl H CO₂ (Ph-4-NO₂) 2-cPr 0 0 1853 ClH CO₂ (Ph-4-NO₂) 2-CH₂CH₂CH₂-3 0 0 1854 Cl H CO₂ (Ph-4-NO₂) 2,6-Me₂ 0 01855 Cl H CO₂ (Ph-4-NO₂) 2-Me, 6-cPr 0 0 1856 Cl H CO₂ (1-Np) 2-Me 0 01857 Cl H CO₂ (1-Np) 2-iPr 0 0 1858 Cl H CO₂ (1-Np) 2-cPr 0 0 1859 Cl HCO₂ (1-Np) 2-CH₂CH₂CH₂-3 0 0 1860 Cl H CO₂ (1-Np) 2,6-Me₂ 0 0 1861 Cl HCO₂ (1-Np) 2-Me, 6-cPr 0 0 1862 Cl H CO₂ (9-Q⁴) 2-Me 0 0 1863 Cl H CO₂(9-Q⁴) 2-iPr 0 0 1864 Cl H CO₂ (9-Q⁴) 2-cPr 0 0 1865 Cl H CO₂ (9-Q⁴)2-CH₂CH₂CH₂-3 0 0 1866 Cl H CO₂ (9-Q⁴) 2,6-Me₂ 0 0 1867 Cl H CO₂ (9-Q⁴)2-Me, 6-cPr 0 0 1868 Cl H CO₂Q⁵ 2-Me 0 0 1869 Cl H CO₂Q⁵ 2-iPr 0 0 1870Cl H CO₂Q⁵ 2-cPr 0 0 1871 Cl H CO₂Q⁵ 2-CH₂CH₂CH₂-3 0 0 1872 Cl H CO₂Q⁵2,6-Me₂ 0 0 1873 Cl H CO₂Q⁵ 2-Me, 6-cPr 0 0 1874 Cl H CONMe₂ 2-Cl 0 01875 Cl H CONMe₂ 2-Br 0 0 1876 Cl H CONMe₂ 2-I 0 0 1877 Cl H CONMe₂ 2-Me0 0 1878 Cl H CONMe₂ 2-iPr 0 0 1879 Cl H CONMe₂ 2-cPr 0 0 1880 Cl HCONMe₂ 2-cBu 0 0 1881 Cl H CONMe₂ 3-CF₃ 0 0 1882 Cl H CONMe₂2-CH₂CH₂CH₂-3 0 0 1883 Cl H CONMe₂ 2-cPr, 5-Me 0 0 1884 Cl H CONMe₂2-OMe, 5-Me 0 0 1885 Cl H CONMe₂ 2-F, 6-iPr 0 0 1886 Cl H CONMe₂ 2-Cl,6-cPr 0 0 1887 Cl H CONMe₂ 2-Br, 6-Me 0 0 1888 Cl H CONMe₂ 2-I, 6-Me 0 01889 Cl H CONMe₂ 2,6-Me₂ 0 0 1890 Cl H CONMe₂ 2-Me, 6-Et 0 0 1891 Cl HCONMe₂ 2-Me, 6-cPr 0 0 1892 Cl H CONMe₂ 2,6-cPr₂ 0 0 1893 Cl H CONMe₂2-cPr, 3,5-Me₂ 0 0 1894 Cl H CONMe₂ 2-cPr, 5,6-Me₂ 0 0 1895 Cl H CONEt₂2-Cl 0 0 1896 Cl H CONEt₂ 2-Br 0 0 1897 Cl H CONEt₂ 2-I 0 0 1898 Cl HCONEt₂ 2-Me 0 0 1899 Cl H CONEt₂ 2-iPr 0 0 1900 Cl H CONEt₂ 2-cPr 0 01901 Cl H CONEt₂ 2-cBu 0 0 1902 Cl H CONEt₂ 2-CH₂CH₂CH₂-3 0 0 1903 Cl HCONEt₂ 2-cPr, 5-Me 0 0 1904 Cl H CONEt₂ 2-OMe, 5-Me 0 0 1905 Cl H CONEt₂2-F, 6-iPr 0 0 1906 Cl H CONEt₂ 2-Cl, 6-cPr 0 0 1907 Cl H CONEt₂ 2-Br,6-Me 0 0 1908 Cl H CONEt₂ 2-I, 6-Me 0 0 1909 Cl H CONEt₂ 2,6-Me₂ 0 01910 Cl H CONEt₂ 2-Me, 6-Et 0 0 1911 Cl H CONEt₂ 2-Me, 6-cPr 0 0 1912 ClH CONEt₂ 2,6-cPr₂ 0 0 1913 Cl H CONEt₂ 2-cPr, 3,5-Me₂ 0 0 1914 Cl HCONEt₂ 2-cPr, 5,6-Me₂ 0 0 1915 Cl H CON(iPr)₂ 2-Me 0 0 1916 Cl HCON(iPr)₂ 2-iPr 0 0 1917 Cl H CON(iPr)₂ 2-cPr 0 0 1918 Cl H CON(iPr)₂2-CH₂CH₂CH₂-3 0 0 1919 Cl H CON(iPr)₂ 2,6-Me₂ 0 0 1920 Cl H CON(iPr)₂2-Me, 6-cPr 0 0 1921 Cl H CO-1-Pyrd 2-Cl 0 0 1922 Cl H CO-1-Pyrd 2-Br 00 1923 Cl H CO-1-Pyrd 2-I 0 0 1924 Cl H CO-1-Pyrd 2-Me 0 0 1925 Cl HCO-1-Pyrd 2-iPr 0 0 1926 Cl H CO-1-Pyrd 2-cPr 0 0 1927 Cl H CO-1-Pyrd2-cBu 0 0 1928 Cl H CO-1-Pyrd 2-CH₂CH₂CH₂-3 0 0 1929 Cl H CO-1-Pyrd2-cPr, 5-Me 0 0 1930 Cl H CO-1-Pyrd 2-OMe, 5-Me 0 0 1931 Cl H CO-1-Pyrd2-F, 6-iPr 0 0 1932 Cl H CO-1-Pyrd 2-Cl, 6-cPr 0 0 1933 Cl H CO-1-Pyrd2-Br, 6-Me 0 0 1934 Cl H CO-1-Pyrd 2-I, 6-Me 0 0 1935 Cl H CO-1-Pyrd2,6-Me₂ 0 0 1936 Cl H CO-1-Pyrd 2-Me, 6-Et 0 0 1937 Cl H CO-1-Pyrd 2-Me,6-cPr 0 0 1938 Cl H CO-1-Pyrd 2,6-cPr₂ 0 0 1939 Cl H CO-1-Pyrd 2-cPr,3,5-Me₂ 0 0 1940 Cl H CO-1-Pyrd 2-cPr, 5,6-Me₂ 0 0 1941 Cl H CONMePh2-Me 0 0 1942 Cl H CONMePh 2-iPr 0 0 1943 Cl H CONMePh 2-cPr 0 0 1944 ClH CONMePh 2-CH₂CH₂CH₂-3 0 0 1945 Cl H CONMePh 2,6-Me₂ 0 0 1946 Cl HCONMePh 2-Me, 6-cPr 0 0 1947 Cl H CONPh₂ 2-Me 0 0 1948 Cl H CONPh₂ 2-iPr0 0 1949 Cl H CONPh₂ 2-cPr 0 0 1950 Cl H CONPh₂ 2-CH₂CH₂CH₂-3 0 0 1951Cl H CONPh₂ 2,6-Me₂ 0 0 1952 Cl H CONPh₂ 2-Me, 6-cPr 0 0 1953 Cl H COSMe2-Me 0 0 1954 Cl H COSMe 2-iPr 0 0 1955 Cl H COSMe 2-cPr 0 0 1956 Cl HCOSMe 2-CH₂CH₂CH₂-3 0 0 1957 Cl H COSMe 2,6-Me₂ 0 0 1958 Cl H COSMe2-Me, 6-cPr 0 0 1959 Cl H COSC₇H₁₅ 2-Me 0 0 1960 Cl H COSC₇H₁₅ 2-iPr 0 01961 Cl H COSC₇H₁₅ 2-cPr 0 0 1962 Cl H COSC₇H₁₅ 2-CH₂CH₂CH₂-3 0 0 1963Cl H COSC₇H₁₅ 2,6-Me₂ 0 0 1964 Cl H COSC₇H₁₅ 2-Me, 6-cPr 0 0 1965 Cl HCOScHx 2-Me 0 0 1966 Cl H COScHx 2-iPr 0 0 1967 Cl H COScHx 2-cPr 0 01968 Cl H COScHx 2-CH₂CH₂CH₂-3 0 0 1969 Cl H COScHx 2,6-Me₂ 0 0 1970 ClH COScHx 2-Me, 6-cPr 0 0 1971 Cl H COSPh 2-Me 0 0 1972 Cl H COSPh 2-iPr0 0 1973 Cl H COSPh 2-cPr 0 0 1974 Cl H COSPh 2-CH₂CH₂CH₂-3 0 0 1975 ClH COSPh 2,6-Me₂ 0 0 1976 Cl H COSPh 2-Me, 6-cPr 0 0 1977 Cl H SO₂Me 2-F0 0 1978 Cl H SO₂Me 2-Cl 0 0 1979 Cl H SO₂Me 2-Br 0 0 1980 Cl H SO₂Me2-I 0 0 1981 Cl H SO₂Me 2-Me 0 0 1982 Cl H SO₂Me 2-Et 0 0 1983 Cl HSO₂Me 2-iPr 0 0 1984 Cl H SO₂Me 2-tBu 0 0 1985 Cl H SO₂Me 2-cPr 0 0 1986Cl H SO₂Me 2-(cPr-1-Me) 0 0 1987 Cl H SO₂Me 2-(cPr-2-Me) 0 0 1988 Cl HSO₂Me 2-(cPr-2,2-Cl₂) 0 0 1989 Cl H SO₂Me 2-cBu 0 0 1990 Cl H SO₂Me2-CH₂CH₂CH₂-3 0 0 1991 Cl H SO₂Me 2-CH═CH—O-3 0 0 1992 Cl H SO₂Me2-CH₂CH₂O-3 0 0 1993 Cl H SO₂Me 2-OCH═CH-3 0 0 1994 Cl H SO₂Me2OCH₂CH₂-3 0 0 1995 Cl H SO₂Me 2-cPr, 5-F 0 0 1996 Cl H SO₂Me 2-cPr,5-Cl 0 0 1997 Cl H SO₂Me 2-cPr, 5-Me 0 0 1998 Cl H SO₂Me 2-OMe, 5-Me 0 01999 Cl H SO₂Me 2-F, 6-iPr 0 0 2000 Cl H SO₂Me 2-F, 6-cPr 0 0 2001 Cl HSO₂Me 2-Cl, 6-Me 0 0 2002 Cl H SO₂Me 2-Cl, 6-cPr 0 0 2003 Cl H SO₂Me2-Br, 6-Me 0 0 2004 Cl H SO₂Me 2-Br, 6-Et 0 0 2005 Cl H SO₂Me 2-Br,6-cPr 0 0 2006 Cl H SO₂Me 2-I, 6-Me 0 0 2007 Cl H SO₂Me 2-I, 6-Et 0 02008 Cl H SO₂Me 2,6-Me₂ 0 0 2009 Cl H SO₂Me 2-Me, 6-Et 0 0 2010 Cl HSO₂Me 2-Me, 6-cPr 0 0 2011 Cl H SO₂Me 2-Et, 6-cPr 0 0 2012 Cl H SO₂Me2-iPr, 6-cPr 0 0 2013 Cl H SO₂Me 2-tBu, 6-cPr 0 0 2014 Cl H SO₂Me2,6-cPr₂ 0 0 2015 Cl H SO₂Me 2-cPr, 6-OMe 0 0 2016 Cl H SO₂Me 2-Br,3,6-Me₂ 0 0 2017 Cl H SO₂Me 2-cPr, 3,5-Me₂ 0 0 2018 Cl H SO₂Me 2-cPr, 4,6-Me₂ 0 0 2019 Cl H SO₂Me 2-Br, 5,6-Me₂ 0 0 2020 Cl H SO₂Me 2-cPr,5,6-Me₂ 0 0 2021 Cl H SO₂Me 2-Br, 5-CH═CH—O-6 0 0 2022 Cl H SO₂Me 2-Me,5-CH₂CH₂CH₂-6 0 0 2023 Cl H SO₂Me 2-Me, 5-CH₂CH₂O-6 0 0 2024 Cl H SO₂Me2-Me, 5-CH═CH—O-6 0 0 2025 Cl H SO₂Me 2-Et, 5-CH₂CH₂CH₂-6 0 0 2026 Cl HSO₂Me 2-cPr, 5-CH₂CH₂CH₂-6 0 0 2027 Cl H SO₂Me 2-cPr, 5-CH═CH—O-6 0 02028 Cl H SO₂Me 2-Br, 3,5,6-Me₃ 0 0 2029 Cl H SO₂Et 2-Me 0 0 2030 Cl HSO₂Et 2-iPr 0 0 2031 Cl H SO₂Et 2-cPr 0 0 2032 Cl H SO₂Et 2-CH₂CH₂CH₂-30 0 2033 Cl H SO₂Et 2,6-Me₂ 0 0 2034 Cl H SO₂Et 2-Me, 6-cPr 0 0 2035 ClH SO₂Pr 2-Cl 0 0 2036 Cl H SO₂Pr 2-Br 0 0 2037 Cl H SO₂Pr 2-I 0 0 2038Cl H SO₂Pr 2-Me 0 0 2039 Cl H SO₂Pr 2-iPr 0 0 2040 Cl H SO₂Pr 2-cPr 0 02041 Cl H SO₂Pr 2-cBu 0 0 2042 Cl H SO₂Pr 2-CH₂CH₂CH₂-3 0 0 2043 Cl HSO₂Pr 2-cPr, 5-Me 0 0 2044 Cl H SO₂Pr 2-OMe, 5-Me 0 0 2045 Cl H SO₂Pr2-F, 6-iPr 0 0 2046 Cl H SO₂Pr 2-Cl, 6-cPr 0 0 2047 Cl H SO₂Pr 2-Br,6-Me 0 0 2048 Cl H SO₂Pr 2-I, 6-Me 0 0 2049 Cl H SO₂Pr 2,6-Me₂ 0 0 2050Cl H SO₂Pr 2-Me, 6-Et 0 0 2051 Cl H SO₂Pr 2-Me, 6-cPr 0 0 2052 Cl HSO₂Pr 2,6-cPr₂ 0 0 2053 Cl H SO₂Pr 2-cPr, 3,5-Me₂ 0 0 2054 Cl H SO₂Pr2-cPr, 5,6-Me₂ 0 0 2055 Cl H SO₂iPr 2-Me 0 0 2056 Cl H SO₂iPr 2-iPr 0 02057 Cl H SO₂iPr 2-cPr 0 0 2058 Cl H SO₂iPr 2-CH₂CH₂CH₂-3 0 0 2059 Cl HSO₂iPr 2,6-Me₂ 0 0 2060 Cl H SO₂iPr 2-Me, 6-cPr 0 0 2061 Cl H SO₂C₈H₁₇2-Me 0 0 2062 Cl H SO₂C₈H₁₇ 2-iPr 0 0 2063 Cl H SO₂C₈H₁₇ 2-cPr 0 0 2064Cl H SO₂C₈H₁₇ 2-CH₂CH₂CH₂-3 0 0 2065 Cl H SO₂C₈H₁₇ 2,6-Me₂ 0 0 2066 Cl HSO₂C₈H₁₇ 2Me, 6-cPr 0 0 2067 Cl H SO₂CH₂Cl 2-Me 0 0 2068 Cl H SO₂CH₂Cl2-iPr 0 0 2069 Cl H SO₂CH₂Cl 2-cPr 0 0 2070 Cl H SO₂CH₂Cl 2-CH₂CH₂CH₂-30 0 2071 Cl H SO₂CH₂Cl 2,6-Me₂ 0 0 2072 Cl H SO₂CH₂Cl 2-Me, 6-cPr 0 02073 Cl H SO₂CF₃ 2-F 0 0 2074 Cl H SO₂CF₃ 2-Cl 0 0 2075 Cl H SO₂CF₃ 2-Br0 0 2076 Cl H SO₂CF₃ 2-I 0 0 2077 Cl H SO₂CF₃ 2-Me 0 0 2078 Cl H SO₂CF₃2-Et 0 0 2079 Cl H SO₂CF₃ 2-iPr 0 0 2080 Cl H SO₂CF₃ 2-tBu 0 0 2081 Cl HSO₂CF₃ 2-cPr 0 0 2082 Cl H SO₂CF₃ 2-(cPr-1-Me) 0 0 2083 Cl H SO₂CF₃2-(cPr-2-Me) 0 0 2084 Cl H SO₂CF₃ 2-(cPr-2,2-Cl₂) 0 0 2085 Cl H SO₂CF₃2-cBu 0 0 2086 Cl H SO₂CF₃ 2-CH₂CH₂CH₂-3 0 0 2087 Cl H SO₂CF₃2-CH═CH—O-3 0 0 2088 Cl H SO₂CF₃ 2-CH₂CH₂O-3 0 0 2089 Cl H SO₂CF₃2-OCH═CH-3 0 0 2090 Cl H SO₂CF₃ 2-OCH₂CH₂-3 0 0 2091 Cl H SO₂CF₃ 2-cPr,5-F 0 0 2092 Cl H SO₂CF₃ 2-cPr, 5-Cl 0 0 2093 Cl H SO₂CF₃ 2-cPr, 5-Me 00 2094 Cl H SO₂CF₃ 2-OMe, 5-Me 0 0 2095 Cl H SO₂CF₃ 2-F, 6-iPr 0 0 2096Cl H SO₂CF₃ 2-F, 6-cPr 0 0 2097 Cl H SO₂CF₃ 2-Cl, 6-Me 0 0 2098 Cl HSO₂CF₃ 2-Cl, 6-cPr 0 0 2099 Cl H SO₂CF₃ 2-Br, 6-Me 0 0 2100 Cl H SO₂CF₃2-Br, 6-Et 0 0 2101 Cl H SO₂CF₃ 2-Br, 6-cPr 0 0 2102 Cl H SO₂CF₃ 2-I,6-Me 0 0 2103 Cl H SO₂CF₃ 2-I, 6-Et 0 0 2104 Cl H SO₂CF₃ 2,6-Me₂ 0 02105 Cl H SO₂CF₃ 2-Me, 6-Et 0 0 2106 Cl H SO₂CF₃ 2-Me, 6-cPr 0 0 2107 ClH SO₂CF₃ 2-Et, 6-cPr 0 0 2108 Cl H SO₂CF₃ 2-iPr, 6-cPr 0 0 2109 Cl HSO₂CF₃ 2-tBu, 6-cPr 0 0 2110 Cl H SO₂CF₃ 2,6-cPr₂ 0 0 2111 Cl H SO₂CF₃2-cPr, 6-OMe 0 0 2112 Cl H SO₂CF₃ 2-Br, 3,6-Me₂ 0 0 2113 Cl H SO₂CF₃2-cPr, 3,5-Me₂ 0 0 2114 Cl H SO₂CF₃ 2-cPr, 4, 6-Me₂ 0 0 2115 Cl H SO₂CF₃2-Br, 5,6-Me₂ 0 0 2116 Cl H SO₂CF₃ 2-cPr, 5,6-Me₂ 0 0 2117 Cl H SO₂CF₃2-Br, 5-CH═CH—O-6 0 0 2118 Cl H SO₂CF₃ 2-Me, 5-CH₂CH₂CH₂-6 0 0 2119 Cl HSO₂CF₃ 2-Me, 5-CH₂CH₂O-6 0 0 2120 Cl H SO₂CF₃ 2-Me, 5-CH═CH—O-6 0 0 2121Cl H SO₂CF₃ 2-Et, 5-CH₂CH₂CH₂-6 0 0 2122 Cl H SO₂CF₃ 2-cPr,5-CH₂CH₂CH₂-6 0 0 2123 Cl H SO₂CF₃ 2-cPr, 5-CH═CH—O-6 0 0 2124 Cl HSO₂CF₃ 2-Br, 3,5,6-Me₃ 0 0 2125 Cl H SO₂CCl₃ 2-Me 0 0 2126 Cl H SO₂CCl₃2-iPr 0 0 2127 Cl H SO₂CCl₃ 2-cPr 0 0 2128 Cl H SO₂CCl₃ 2-CH₂CH₂CH₂-3 00 2129 Cl H SO₂CCl₃ 2,6-Me₂ 0 0 2130 Cl H SO₂CCl₃ 2-Me, 6-cPr 0 0 2131Cl H SO₂CH₂CF₃ 2-Me 0 0 2132 Cl H SO₂CH₂CF₃ 2-iPr 0 0 2133 Cl HSO₂CH₂CF₃ 2-cPr 0 0 2134 Cl H SO₂CH₂CF₃ 2-CH₂CH₂CH₂-3 0 0 2135 Cl HSO₂CH₂CF₃ 2,6-Me₂ 0 0 2136 Cl H SO₂CH₂CF₃ 2-Me, 6-cPr 0 0 2137 Cl HSO₂CH₂CH₂CH₂Cl 2-Me 0 0 2138 Cl H SO₂CH₂CH₂CH₂Cl 2-iPr 0 0 2139 Cl HSO₂CH₂CH₂CH₂Cl 2-cPr 0 0 2140 Cl H SO₂CH₂CH₂CH₂Cl 2-CH₂CH₂CH₂-3 0 0 2141Cl H SO₂CH₂CH₂CH₂Cl 2,6-Me₂ 0 0 2142 Cl H SO₂CH₂CH₂CH₂Cl 2-Me, 6-cPr 0 02143 Cl H SO₂Ph 2-F 0 0 2144 Cl H SO₂Ph 2-Cl 0 0 2145 Cl H SO₂Ph 2-Br 00 2146 Cl H SO₂Ph 2-I 0 0 2147 Cl H SO₂Ph 2-Me 0 0 2148 Cl H SO₂Ph 2-Et0 0 2149 Cl H SO₂Ph 2-iPr 0 0 2150 Cl H SO₂Ph 2-tBu 0 0 2151 Cl H SO₂Ph2-cPr 0 0 2152 Cl H SO₂Ph 2-(cPr-1-Me) 0 0 2153 Cl H SO₂Ph 2-(cPr-2-Me)0 0 2154 Cl H SO₂Ph 2-(cPr-2,2-Cl₂) 0 0 2155 Cl H SO₂Ph 2-cBu 0 0 2156Cl H SO₂Ph 2-CH₂CH₂CH₂-3 0 0 2157 Cl H SO₂Ph 2-CH═CHO-3 0 0 2158 Cl HSO₂Ph 2-CH₂CH₂O-3 0 0 2159 Cl H SO₂Ph 2-OCH═CH-3 0 0 2160 Cl H SO₂Ph2-OCH₂CH₂-3 0 0 2161 Cl H SO₂Ph 2-cPr, 5-F 0 0 2162 Cl H SO₂Ph 2-cPr,5-Cl 0 0 2163 Cl H SO₂Ph 2-cPr, 5-Me 0 0 2164 Cl H SO₂Ph 2-OMe, 5-Me 0 02165 Cl H SO₂Ph 2-F, 6-iPr 0 0 2166 Cl H SO₂Ph 2-F, 6-cPr 0 0 2167 Cl HSO₂Ph 2-Cl, 6-Me 0 0 2168 Cl H SO₂Ph 2-Cl, 6-cPr 0 0 2169 Cl H SO₂Ph2-Br, 6-Me 0 0 2170 Cl H SO₂Ph 2-Br, 6-Et 0 0 2171 Cl H SO₂Ph 2-Br,6-cPr 0 0 2172 Cl H SO₂Ph 2-I, 6-Me 0 0 2173 Cl H SO₂Ph 2-I, 6-Et 0 02174 Cl H SO₂Ph 2,6-Me₂ 0 0 2175 Cl H SO₂Ph 2-Me, 6-Et 0 0 2176 Cl HSO₂Ph 2-Me, 6-cPr 0 0 2177 Cl H SO₂Ph 2-Et, 6-cPr 0 0 2178 Cl H SO₂Ph2-iPr, 6-cPr 0 0 2179 Cl H SO₂Ph 2-tBu, 6-cPr 0 0 2180 Cl H SO₂Ph2,6-cPr₂ 0 0 2181 Cl H SO₂Ph 2-cPr, 6-OMe 0 0 2182 Cl H SO₂Ph 2-Br,3,6-Me₂ 0 0 2183 Cl H SO₂Ph 2-cPr, 3,5-Me₂ 0 0 2184 Cl H SO₂Ph 2-cPr, 4,6-Me₂ 0 0 2185 Cl H SO₂Ph 2-Br, 5,6-Me₂ 0 0 2186 Cl H SO₂Ph 2-cPr,5,6-Me₂ 0 0 2187 Cl H SO₂Ph 2-Br, 5-CH═CH—O-6 0 0 2188 Cl H SO₂Ph 2-Me,5-CH₂CH₂CH₂-6 0 0 2189 Cl H SO₂Ph 2-Me, 5-CH₂CH₂O-6 0 0 2190 Cl H SO₂Ph2-Me, 5-CH═CH—O-6 0 0 2191 Cl H SO₂Ph 2-Et, 5-CH₂CH₂CH₂-6 0 0 2192 Cl HSO₂Ph 2-cPr, 5-CH₂CH₂CH₂-6 0 0 2193 Cl H SO₂Ph 2-cPr, 5-CH═CH—O-6 0 02194 Cl H SO₂Ph 2-Br, 3,5,6-Me₃ 0 0 2195 Cl H SO₂ (Ph-4-Cl) 2-Cl 0 02196 Cl H SO₂ (Ph-4-Cl) 2-Br 0 0 2197 Cl H SO₂ (Ph-4-cl) 2-I 0 0 2198 ClH SO₂ (Ph-4-Cl) 2-Me 0 0 2199 Cl H SO₂ (Ph-4-Cl) 2-iPr 0 0 2200 Cl H SO₂(Ph-4-Cl) 2-tBu 0 0 2201 Cl H SO₂ (Ph-4-Cl) 2-cPr 0 0 2202 Cl H SO₂(Ph-4-Cl) 2-cBu 0 0 2203 Cl H SO₂ (Ph-4-Cl) 2-CH₂CH₂CH₂-3 0 0 2204 Cl HSO₂ (Ph-4-Cl) 2-cPr, 5-Me 0 0 2205 Cl H SO₂ (Ph-4-Cl) 2-OMe, 5-Me 0 02206 Cl H SO₂ (Ph-4-Cl) 2-F, 6-iPr 0 0 2207 Cl H SO₂ (Ph-4-Cl) 2-Cl,6-cPr 0 0 2208 Cl H SO₂ (Ph-4-Cl) 2-Br, 6-Me 0 0 2209 Cl H SO₂ (Ph-4-Cl)2-I, 6-Me 0 0 2210 Cl H SO₂ (Ph-4-Cl) 2,6-Me₂ 0 0 2211 Cl H SO₂(Ph-4-Cl) 2-Me, 6-Et 0 0 2212 Cl H SO₂ (Ph-4-Cl) 2-Me, 6-cPr 0 0 2213 ClH SO₂ (Ph-4-Cl) 2,6-cPr₂ 0 0 2214 Cl H SO₂ (Ph-4-Cl) 2-cPr, 3,5-Me₂ 0 02215 Cl H SO₂ (Ph-4-Cl) 2-cPr, 5,6-Me₂ 0 0 2216 Cl H SO₂ (Ph-4-Me) 2-F 00 2217 Cl H SO₂ (Ph-4-Me) 2-Cl 0 0 2218 Cl H SO₂ (Ph-4-Me) 2-Br 0 0 2219Cl H SO₂ (Ph-4-Me) 2-I 0 0 2220 Cl H SO₂ (Ph-4-Me) 2-Me 0 0 2221 Cl HSO₂ (Ph-4-Me) 2-Et 0 0 2222 Cl H SO₂ (Ph-4-Me) 2-iPr 0 0 2223 Cl H SO₂(Ph-4-Me) 2-sBu 0 0 2224 Cl H SO₂ (Ph-4-Me) 2-tBu 0 0 2225 Cl H SO₂(Ph-4-Me) 2-cPr 0 0 2226 Cl H SO₂ (Ph-4-Me) 2-(cPr-1-Me) 0 0 2227 Cl HSO₂ (Ph-4-Me) 2-(cPr-2-Me) 0 0 2228 Cl H SO₂ (Ph-4-Me) 2-(cPr-2,2-Cl₂) 00 2229 Cl H SO₂ (Ph-4-Me) 2-cBu 0 0 2230 Cl H SO₂ (Ph-4-Me) 2-cHx 0 02231 Cl H SO₂ (Ph-4-Me) 2-Ph 0 0 2232 Cl H SO₂ (Ph-4-Me) 2-OMe 0 0 2233Cl H SO₂ (Ph-4-Me) 2-OSO₂ (Ph-4-Me) 0 0 2234 Cl H SO₂ (Ph-4-Me) 3-Cl 0 02235 Cl H SO₂ (Ph-4-Me) 3-tBu 0 0 2236 Cl H SO₂ (Ph-4-Me) 3-CF₃ 0 0 2237Cl H SO₂ (Ph-4-Me) 3-CN 0 0 2238 Cl H SO₂ (Ph-4-Me) 3-OMe 0 0 2239 Cl HSO₂ (Ph-4-Me) 2-CH₂CH₂CH₂-3 0 0 2240 Cl H SO₂ (Ph-4-Me) 2-CH═CH═CH═CH-30 0 2241 Cl H SO₂ (Ph-4-Me) 2-CH═CH—O-3 0 0 2242 Cl H SO₂ (Ph-4-Me)2-CH₂CH₂O-3 0 0 2243 Cl H SO₂ (Ph-4-Me) 2-OCH═CH-3 0 0 2244 Cl H SO₂(Ph-4-Me) 2-OCH₂CH₂-3 0 0 2245 Cl H SO₂ (Ph-4-Me) 2-Br, 4-tBu 0 0 2246Cl H SO₂ (Ph-4-Me) 2-Me, 4-Cl 0 0 2247 Cl H SO₂ (Ph-4-Me) 2, 4-Me₂ 0 02248 Cl H SO₂ (Ph-4-Me) 2-iPr, 4-Br 0 0 2249 Cl H SO₂ (Ph-4-Me) 2-iPr,5-Me 0 0 2250 Cl H SO₂ (Ph-4-Me) 2-cPr, 5-F 0 0 2251 Cl H SO₂ (Ph-4-Me)2-cPr, 5-Cl 0 0 2252 Cl H SO₂ (Ph-4-Me) 2-cPr, 5-Me 0 0 2253 Cl H SO₂(Ph-4-Me) 2-OMe, 5-Me 0 0 2254 Cl H SO₂ (Ph-4-Me) 2-F, 6-iPr 0 0 2255 ClH SO₂ (Ph-4-Me) 2-F, 6-cPr 0 0 2256 Cl H SO₂ (Ph-4-Me) 2-Cl, 6-Me 0 02257 Cl H SO₂ (Ph-4-Me) 2-Cl, 6-cPr 0 0 2258 Cl H SO₂ (Ph-4-Me) 2-Br,6-Me 0 0 2259 Cl H SO₂ (Ph-4-Me) 2-Br, 6-Et 0 0 2260 Cl H SO₂ (Ph-4-Me)2-Br, 6-cPr 0 0 2261 Cl H SO₂ (Ph-4-Me) 2-I, 6-Me 0 0 2262 Cl H SO₂(Ph-4-Me) 2-I, 6-Et 0 0 2263 Cl H SO₂ (Ph-4-Me) 2,6-Me₂ 0 0 2264 Cl HSO₂ (Ph-4-Me) 2-Me, 6-Et 0 0 2265 Cl H SO₂ (Ph-4-Me) 2-Me, 6-cPr 0 02266 Cl H SO₂ (Ph-4-Me) 2-Et, 6-cPr 0 0 2267 Cl H SO₂ (Ph-4-Me) 2-iPr,6-cPr 0 0 2268 Cl H SO₂ (Ph-4-Me) 2-tBu, 6-cPr 0 0 2269 Cl H SO₂(Ph-4-Me) 2,6-cPr₂ 0 0 2270 Cl H SO₂ (Ph-4-Me) 2-cPr, 6-OMe 0 0 2271 ClH SO₂ (Ph-4-Me) 2-Br, 3,6-Me₂ 0 0 2272 Cl H SO₂ (Ph-4-Me) 2-cPr, 3,5-Me₂0 0 2273 Cl H SO₂ (Ph-4-Me) 2-cPr, 4, 6-Me₂ 0 0 2274 Cl H SO₂ (Ph-4-Me)2-Br, 5,6-Me₂ 0 0 2275 Cl H SO₂ (Ph-4-Me) 2-cPr, 5,6-Me₂ 0 0 2276 Cl HSO₂ (Ph-4-Me) 2-Br, 5-CH═CH—O-6 0 0 2277 Cl H SO₂ (Ph-4-Me) 2-Me,5-CH₂CH₂CH₂-6 0 0 2278 Cl H SO₂ (Ph-4-Me) 2-Me, 5-CH₂CH₂O-6 0 0 2279 ClH SO₂ (Ph-4-Me) 2-Me, 5-CH═CH—O-6 0 0 2280 Cl H SO₂ (Ph-4-Me) 2-Et,5-CH₂CH₂CH₂-6 0 0 2281 Cl H SO₂ (Ph-4-Me) 2-cPr, 5-CH₂CH₂CH₂-6 0 0 2282Cl H SO₂ (Ph-4-Me) 2-cPr, 5-CH═CH—O-6 0 0 2283 Cl H SO₂ (Ph-4-Me) 2-Br,3,5,6-Me₃ 0 0 2284 Cl H SO₂ (Ph-4-No2) 2-Cl 0 0 2285 Cl H SO₂ (Ph-4-NO₂)2-Br 0 0 2286 Cl H SO₂ (Ph-4-NO₂) 2-I 0 0 2287 Cl H SO₂ (Ph-4-NO₂) 2-Me0 0 2288 Cl H SO₂ (Ph-4-NO₂) 2-iPr 0 0 2289 Cl H SO₂ (Ph-4-NO₂) 2-cPr 00 2290 Cl H SO₂ (Ph-4-NO₂) 2-cBu 0 0 2291 Cl H SO₂ (Ph-4-NO₂)2-CH₂CH₂CH₂-3 0 0 2292 Cl H SO₂ (Ph-4-NO₂) 2-cPr, 5-Me 0 0 2293 Cl H SO₂(Ph-4-NO₂) 2-OMe, 5-Me 0 0 2294 Cl H SO₂ (Ph-4-NO₂) 2-F, 6-iPr 0 0 2295Cl H SO₂ (Ph-4-NO₂) 2-Cl, 6-cPr 0 0 2296 Cl H SO₂ (Ph-4-NO2) 2-Br, 6-Me0 0 2297 Cl H SO₂ (Ph-4-NO₂) 2-I, 6-Me 0 0 2298 Cl H SO₂ (Ph-4-NO₂)2,6-Me₂ 0 0 2299 Cl H SO₂ (Ph-4-NO₂) 2-Me, 6-Et 0 0 2300 Cl H SO₂(Ph-4-NO₂) 2-Me, 6-cPr 0 0 2301 Cl H SO₂ (Ph-4-NO₂) 2,6-cPr₂ 0 0 2302 ClH SO₂ (Ph-4-NO₂) 2-cPr, 3,5-Me₂ 0 0 2303 Cl H SO₂ (Ph-4-NO₂) 2-cPr,5,6-Me₂ 0 0 2304 Cl H SO₂ (Ph-4-OMe) 2-Me 0 0 2305 Cl H SO₂ (Ph-4-OMe)2-iPr 0 0 2306 Cl H SO₂ (Ph-4-OMe) 2-cPr 0 0 2307 Cl H SO₂ (Ph-4-OMe)2-CH₂CH₂CH₂-3 0 0 2308 Cl H SO₂ (Ph-4-OMe) 2,6-Me₂ 0 0 2309 Cl H SO₂(Ph-4-OMe) 2-Me, 6-cPr 0 0 2310 Cl H SO₂ (Ph-2,4,6-Me₃) 2-Me 0 0 2311 ClH SO₂ (Ph-2,4,6-Me₃) 2-iPr 0 0 2312 Cl H SO₂ (Ph-2,4,6-Me₃) 2-cPr 0 02313 Cl H SO₂ (Ph-2,4,6-Me₃) 2-CH₂CH₂CH₂-3 0 0 2314 Cl H SO₂(Ph-2,4,6-Me₃) 2,6-Me₂ 0 0 2315 Cl H SO₂ (Ph-2,4,6-Me₃) 2-Me, 6-cPr 0 02316 Cl H SO₂ (Ph-2,4,6-iPr₃) 2-Me 0 0 2317 Cl H SO₂ (Ph-2,4,6-iPr₃)2-iPr 0 0 2318 Cl H SO₂ (Ph-2,4,6-iPr₃) 2-cPr 0 0 2319 Cl H SO₂(Ph-2,4,6-iPr₃) 2-CH₂CH₂CH₂-3 0 0 2320 Cl H SO₂ (Ph-2,4,6-iPr₃) 2,6-Me₂0 0 2321 Cl H SO₂ (Ph-2,4,6-iPr₃) 2-Me, 6-cPr 0 0 2322 Cl H SO₂(Ph-2-SO₂OQ⁵) 2-Me 0 0 2323 Cl H SO₂ (Ph-2-SO₂OQ⁵) 2-iPr 0 0 2324 Cl HSO₂ (Ph-2-SO₂OQ⁵) 2-cPr 0 0 2325 Cl H SO₂ (Ph-2-SO₂OQ⁵) 2-CH₂CH₂CH₂-3 00 2326 Cl H SO₂ (Ph-2-SO₂OQ⁵) 2,6-Me₂ 0 0 2327 Cl H SO₂ (Ph-2-SO₂OQ⁵)2-Me, 6-cPr 0 0 2328 Cl H SO₂ (Ph-3-SO₂OQ⁵) 2-Me 0 0 2329 Cl H SO₂(Ph-3-SO₂OQ⁵) 2-iPr 0 0 2330 Cl H SO₂ (Ph-3-SO₂OQ⁵) 2-cPr 0 0 2331 Cl HSO₂ (Ph-3-SO₂OQ⁵) 2-CH₂CH₂CH₂-3 0 0 2332 Cl H SO₂ (Ph-3-SO₂OQ⁵) 2,6-Me₂0 0 2333 Cl H SO₂ (Ph-3-SO₂OQ⁵) 2-Me, 6-cPr 0 0 2334 Cl H SO₂(Ph-4-SO₂OQ⁵) 2-Me 0 0 2335 Cl H SO₂ (Ph-4-SO₂OQ⁵) 2-iPr 0 0 2336 Cl HSO₂ (Ph-4-SO₂OQ⁵) 2-cPr 0 0 2337 Cl H SO₂ (Ph-4-SO₂OQ⁵) 2-CH₂CH₂CH₂-3 00 2338 Cl H SO₂ (Ph-4-SO₂OQ⁵) 2,6-Me₂ 0 0 2339 Cl H SO₂ (Ph-4-SO₂OQ⁵)2-Me, 6-cPr 0 0 2340 Cl H SO₂OQ⁵ 2-Me 0 0 2341 Cl H SO₂OQ⁵ 2-iPr 0 02342 Cl H SO₂OQ⁵ 2-cPr 0 0 2343 Cl H SO₂OQ⁵ 2-CH₂CH₂CH₂-3 0 0 2344 Cl HSO₂OQ⁵ 2,6-Me₂ 0 0 2345 Cl H SO₂OQ⁵ 2-Me, 6-cPr 0 0 2346 Cl H SO₂NMe₂2-Cl 0 0 2347 Cl H SO₂NMe₂ 2-Br 0 0 2348 Cl H SO₂NMe₂ 2-I 0 0 2349 Cl HSO₂NMe₂ 2-Me 0 0 2350 Cl H SO₂NMe₂ 2-iPr 0 0 2351 Cl H SO₂NMe₂ 2-cPr 0 02352 Cl H SO₂NMe₂ 2-cBu 0 0 2353 Cl H SO₂NMe₂ 2-CH₂CH₂CH₂-3 0 0 2354 ClH SO₂NMe₂ 2-cPr, 5-Me 0 0 2355 Cl H SO₂NMe₂ 2-OMe, 5-Me 0 0 2356 Cl HSO₂NMe₂ 2-F, 6-iPr 0 0 2357 Cl H SO₂NMe₂ 2-Cl, 6-cPr 0 0 2358 Cl HSO₂NMe₂ 2-Br, 6-Me 0 0 2359 Cl H SO₂NMe₂ 2-I, 6-Me 0 0 2360 Cl H SO₂NMe₂2,6-Me₂ 0 0 2361 Cl H SO₂NMe₂ 2-Me, 6-Et 0 0 2362 Cl H SO₂NMe₂ 2-Me,6-cPr 0 0 2363 Cl H SO₂NMe₂ 2,6-cPr₂ 0 0 2364 Cl H SO₂NMe₂ 2-cPr,3,5-Me₂ 0 0 2365 Cl H SO₂NMe 2-cPr, 5,6-Me₂ 0 0 2366 Cl H SO₂OEt 2-Me 00 2367 Cl H SO₂OEt 2-iPr 0 0 2368 Cl H SO₂OEt 2-cPr 0 0 2369 Cl H SO₂OEt2-CH₂CH₂CH₂-3 0 0 2370 Cl H SO₂OEt 2,6-Me₂ 0 0 2371 Cl H SO₂OEt 2-Me,6-cPr 0 0 2372 Cl Me H 2-Me 0 0 2373 Cl Me H 2-iPr 0 0 2374 Cl Me H2-cPr 0 0 2375 Cl Me H 2-CH₂CH₂CH₂-3 0 0 2376 Cl Me H 2,6-Me₂ 0 0 2377Cl Me H 2-Me, 6-cPr 0 0 2378 Cl CH₂OMe H 2-Me 0 0 2379 Cl CH₂OMe H 2-iPr0 0 2380 Cl CH₂OMe H 2-cPr 0 0 2381 Cl CH₂OMe H 2-CH₂CH₂CH₂-3 0 0 2382Cl CH₂OMe H 2,6-Me₂ 0 0 2383 Cl CH₂OMe H 2-Me, 6-cPr 0 0 2384 Cl CO₂Et H2-Me 0 0 2385 Cl CO₂Et H 2-iPr 0 0 2386 Cl CO₂Et H 2-tBu 0 0 2387 ClCO₂Et H 2-cPr 0 0 2388 Cl CO₂Et H 2-CH₂CH₂CH₂-3 0 0 2389 Cl CO₂Et H2,6-Me₂ 0 0 2390 Cl CO₂Et H 2-Me, 6-cPr 0 0 2391 Cl CO(Ph-2-F) H 2-tBu 00 2392 Cl OMe H 2-Me 0 0 2393 Cl O(Ph-2,4-F₂) H 2,4-F₂ 0 0 2394 ClO(Ph-2,6-F₂) H 2,6-F₂ 0 0 2395 Cl O(Ph-2-Me) H 2-Me 0 0 2396 ClO(Ph-2-Me) H 2-iPr 0 0 2397 Cl O(Ph-2-Me) H 2-cPr 0 0 2398 Cl O(Ph-2-Me)H 2-CH₂CH₂CH₂-3 0 0 2399 Cl O(Ph-2-Me) H 2,6-Me₂ 0 0 2400 Cl O(Ph-2-Me)H 2-Me, 6-cPr 0 0 2401 Cl SPh H 2-Me 0 0 2402 Cl SiMe₃ H H 0 0 2403 ClSiMe₃ H 2-Me 0 0 2404 Cl SiMe₃ H 2-iPr 0 0 2405 Cl SiMe₃ H 2-tBu 0 02406 Cl SiMe₃ H 2-cPr 0 0 2407 Cl SiMe₃ H 2-CH₂CH₂CH₂-3 0 0 2408 ClSiMe₃ H 2,6-Me₂ 0 0 2409 Cl SiMe₃ H 2-Me, 6-cPr 0 0 2410 Br H H 2-Cl 0 02411 Br H H 2-Me 0 0 2412 Br H H 2-iPr 0 0 2413 Br H H 2-cPr 0 0 2414 BrH H 2-CH₂CH₂CH₂-3 0 0 2415 Br H H 2,6-Me₂ 0 0 2416 Br H H 2-Me, 6-cPr 00 2417 Me H H 2-Me 0 0 2418 Me H H 2-iPr 0 0 2419 Me H H 2-cPr 0 0 2420Me H H 2-CH₂CH₂CH₂-3 0 0 2421 Me H H 2,6-Me₂ 0 0 2422 Me H H 2-Me, 6-cPr0 0 2423 cPr H H 2-Me 0 0 2424 cPr H H 2-iPr 0 0 2425 cPr H H 2-cPr 0 02426 cPr H H 2-CH₂CH₂CH₂-3 0 0 2427 cPr H H 2,6-Me₂ 0 0 2428 cPr H H2-Me, 6-cPr 0 0 2429 CF₃ H H 2-Cl 0 0 2430 CF₃ H H 2-Me 0 0 2431 CF₃ H H2-iPr 0 0 2432 CF₃ H H 2-cPr 0 0 2433 CF₃ H H 2-CH₂CH₂CH₂-3 0 0 2434 CF₃H H 2,6-Me₂ 0 0 2435 CF₃ H H 2-Me, 6-cPr 0 0 2436 CH═CH₂ H H 2-Me 0 02437 CH═CH₂ H H 2-iPr 0 0 2438 CH═CH₂ H H 2-cPr 0 0 2439 CH═CH₂ H H2-CH₂CH₂CH₂-3 0 0 2440 CH═CH₂ H H 2,6-Me₂ 0 0 2441 CH═CH₂ H H 2-Me,6-cPr 0 0 2442 CH═CHMe H H 2-Me 0 0 2443 CH═CHMe H H 2-iPr 0 0 2444CH═CHMe H H 2-cPr 0 0 2445 CH═CHMe H H 2-CH₂CH₂CH₂-3 0 0 2446 CH═CHMe HH 2,6-Me₂ 0 0 2447 CH═CHMe H H 2-Me, 6-cPr 0 0 2448 CH₂CH═CH₂ H H 2-Me 00 2449 CN H H 2-Me 0 0 2450 CN H H 2-iPr 0 0 2451 CN H H 2-cPr 0 0 2452CN H H 2-CH₂CH₂CH₂-3 0 0 2453 CN H H 2,6-Me₂ 0 0 2454 CN H H 2-Me, 6-cPr0 0 2455 COMe H H 2-Me 0 0 2456 COMe H H 2-iPr 0 0 2457 COMe H H 2-cPr 00 2458 COMe H H 2-CH₂CH₂CH₂-3 0 0 2459 COMe H H 2,6-Me₂ 0 0 2460 COMe HH 2-Me, 6-cPr 0 0 2461 COBu H H 2,6-Me₂ 0 0 2462 CONMe₂ H H 2,6-Me₂ 0 02463 CONMe₂ SiMe₃ H 2,6-Me₂ 0 0 2464 Ph H H 2-Me 0 0 2465 Ph H H 2-iPr 00 2466 Ph H H 2-cPr 0 0 2467 Ph H H 2-CH₂CH₂CH₂-3 0 0 2468 Ph H H2,6-Me₂ 0 0 2469 Ph H H 2-Me, 6-cPr 0 0 2470 Ph H H 3-CN 0 0 2471Ph-3-CF₃ H H 2-Me 0 0 2472 Ph-3-CN H H 2-iPr 0 0 2473 Ph-3-CN H H 2-cPr0 0 2474 Ph-3-CN H H 2-CH₂CH₂CH₂-3 0 0 2475 Ph-3-CN H H 2,6-Me₂ 0 0 2476Ph-3-CN H H 2-Me, 6-cPr 0 0 2477 2-Fur H H 2-Me 0 0 2478 2-Thi H H 2-Me0 0 2479 2-Thi H H 2-iPr 0 0 2480 2-Thi H H 2-cPr 0 0 2481 2-Thi H H2-CH₂CH₂CH₂-3 0 0 2482 2-Thi H H 2,6-Me₂ 0 0 2483 2-Thi H H 2-Me, 6-cPr0 0 2484 OMe H H 2-Me 0 0 2485 O(Ph-2-F) H H 2-F 0 0 2486 O(Ph-2-F) H H2-Me 0 0 2487 O(Ph-2-F) H H 2-iPr 0 0 2488 O(Ph-2-F) H H 2-cPr 0 0 2489O(Ph-2-F) H H 2-CH₂CH₂CH₂-3 0 0 2490 O(Ph-2-F) H H 2,6-Me₂ 0 0 2491O(Ph-2-F) H H 2-Me, 6-cPr 0 0 2492 O(Ph-2-Me) H H 2-Me 0 0 2493O(Ph-2-Me) H H 2-iPr 0 0 2494 O(Ph-2-Me) H H 2-cPr 0 0 2495 O(Ph-2-Me) HH 2-CH₂CH₂CH₂-3 0 0 2496 O(Ph-2-Me) H H 2,6-Me₂ 0 0 2497 O(Ph-2-Me) H H2-Me, 6-cPr 0 0 2498 O(Ph-2-Me) CO₂Et H 2-Me 0 0 2499 O(Ph-4-tBu) H H4-tBu 0 0 2500 O(Ph-2-iPr-5-Me) H H 2-iPr, 5-Me 0 0 2501 O(Ph-2,3,5-Me₃)H H 2,3,5-Me₃ 0 0 2502 O(Ph-2,4,6-Me₃) H H 2,4,6-Me₃ 0 0 2503O(Ph-2-cHx) H H 2-cHx 0 0 2504 O(Ph-3-cN) H H 3-CN 0 0 2505O(Ph-4-SiMe₃) H H 4-SiMe₃ 0 0 2506 OQ⁵ H H 2-Me 0 0 2507 OQ⁵ H H 2-iPr 00 2508 OQ⁵ H H 2-cPr 0 0 2509 OQ⁵ H H 2-CH₂CH₂CH₂-3 0 0 2510 OQ⁵ H H2,6-Me₂ 0 0 2511 OQ⁵ H H 2-Me, 6-cPr 0 0 2512 Cl H H 2-(cPr-1-F-2-F) 0 02513 Cl H H 2-(cPr-1-F-2-Cl) 0 0 2514 Cl H H 2-(cPr-1,2-Cl₂) 0 0 2515 ClH H 2-(cPr-1-Cl-2-Br) 0 0 2516 Cl H H 2-(cPr-1,2-Br₂) 0 0 2517 Cl H H2-(cPr-1-Me-2-Cl) 0 0 2518 Cl H H 2-(cPr-1-Me-2-Br) 0 0 2519 Cl H H2-(cPr-2-F-2-Cl) 0 0 2520 Cl H H 2-(cPr-2-F-2-Br) 0 0 2521 Cl H H2-(cPr-2-Cl-2-Br) 0 0 2522 Cl H H 2-(cPr-1-Me-2,2-Cl₂) 0 0 2523 Cl H H2-(cPr-1-Me-2,2-Br₂) 0 0 2524 Cl H H 2-(cPr-1-Me-2-F-2-Cl) 0 0 2525 Cl HH 2-C(F)═CH₂ 0 0 2526 Cl H H 2-C(Cl)═CH₂ 0 0 2527 Cl H H 2-C(Br)═CH₂ 0 02528 Cl H H 2-C(Et)═CH₂ 0 0 2529 Cl H H 2-C(iPr)═CH₂ 0 0 2530 Cl H H2-C(tBu)═CH₂ 0 0 2531 Cl H H 2-C(CN)═CH₂ 0 0 2532 Cl H H 2-CH═CHF 0 02533 Cl H H 2-CH═CHCl 0 0 2534 Cl H H 2-CH═CHBr 0 0 2535 Cl H H2-CCl═CHC 0 0 2536 Cl H H 2-CMe═CHCl 0 0 2537 Cl H H 2-CH═CF₂ 0 0 2538Cl H H 2-CH═CCl₂ 0 0 2539 Cl H H 2-CH═CBr₂ 0 0 2540 Cl H H 2-CH═CMe₂ 0 02541 Cl H H 2-CCl═CCl₂ 0 0 2542 Cl H H 2-CMe═CMe₂ 0 0 2543 Cl H H2-CH═C(CN)₂ 0 0 2544 Cl H H 3-OH 0 0 2545 Cl H H 4-OH 0 0 2546 Cl H H2-OCH₂Ph 0 0 2547 Cl H H 3-OCH₂Ph 0 0 2548 Cl H H 4-OCH₂Ph 0 0 2549 Cl HH 2-I, 3-F 0 0 2550 Cl H H 2-I, 3-Me 0 0 2551 Cl H H 2-I, 3-OMe 0 0 2552Cl H H 2-CHMeCH₂-3 0 0 2553 Cl H H 2-CMe₂CH₂-3 0 0 2554 Cl H H2-CH₂CHMe-3 0 0 2555 Cl H H 2-CH₂CH{(CH₂)₃OH}-3 0 0 2556 Cl H H2-CH₂CMe₂-3 0 0 2557 Cl H H 2-CH(CH₂)CH-3 0 0 2558 Cl H H2-CH(—CH₂CH₂—)CH₂-3 0 0 2559 Cl H H 2-CHOMeCH₂-3 0 0 2560 Cl H H2-C(═O)CH₂-3 0 0 2561 Cl H H 2-CH₂C(═O)-3 0 0 2562 Cl H H 2-C(═O)C(═O)-30 0 2563 Cl H H 2-CH₂CH₂NMe-3 0 0 2564 Cl H H 2-CH═CHNH-3 0 0 2565 Cl HH 2-CH═CHNMe-3 0 0 2566 Cl H H 2-NMeCH₂CH₂-3 0 0 2567 Cl H H 2-NHCH═CH-30 0 2568 Cl H H 2-NMeCH═CH-3 0 0 2569 Cl H H 2-N(COMe)CH═CH-3 0 0 2570Cl H H 2-Me, 4-COMe 0 0 2571 Cl H H 2-Me, 4-C(═NOMe)Me 0 0 2572 Cl H H2-Me, 4-OCOMe 0 0 2573 Cl H H 2-Me, 4-OCOPh 0 0 2574 Cl H H 2-OMe,5-CO₂Me 0 0 2575 Cl H H 2-Me, 6-CH₂F 0 0 2576 Cl H H 2-Me, 6-CHF₂ 0 02577 Cl H H 2-Me, 6-CMe═CH₂ 0 0 2578 Cl H H 2-Me, 6-COMe 0 0 2579 Cl H H2-Me, 6-C(═NOMe)Me 0 0 2580 Cl H H 2-OMe, 6-CO₂Me 0 0 2581 Cl H H 2-Me,6-OCOMe 0 0 2582 Cl H H 2-Me, 6-OCOPh 0 0 2583 Cl H H 3-Me, 4-F 0 0 2584Cl H H 3-CH₂CH₂CH₂-4 0 0 2585 Cl H H 3-CH₂CH₂CMe₂-4 0 0 2586 Cl H H2,6-Me₂, 3-Br 0 0 2587 Cl H H 2-Me, 3-Br, 6-cPr 0 0 2588 Cl H H 2,6-Me₂,3-NO₂ 0 0 2589 Cl H H 2-Me, 3-NO₂,6-cPr 0 0 2590 Cl H H 6-Cl,2-CH₂OCH₂-3 0 0 2591 Cl H H 6-Br, 2-CH₂OCH₂-3 0 0 2592 Cl H H 6-Me,2-CH₂OCH₂-3 0 0 2593 Cl H H 6-Et, 2-CH₂OCH₂-3 0 0 2594 Cl H H 6-iPr,2-CH₂OCH₂-3 0 0 2595 Cl H H 6-cPr, 2-CH₂OCH₂-3 0 0 2596 Cl H H 2,4-Br₂,5-SEt 0 0 2597 Cl H H 2-F, 3,5,6-Me₃ 0 0 2598 Cl H H 2,3,5,6-Cl₄ 0 02599 Cl H H 2-Cl, 3,5,6-Me₃ 0 0 2600 Cl H H 2-I, 3,5,6-Me₃ 0 0 2601 Cl HH 2,3,3,6-Et 0 0 2602 Cl H H 2,3,5-Me₃, 6-iPr 0 0 2603 Cl H H 2,3,5-Me₃,6-CH═CH₂ 0 0 2604 Cl H H 2,3,5-Me₃, 6-CCl═CH₂ 0 0 2605 Cl H H 2,3,5-Me₃,6-CMe═CH₂ 0 0 2606 Cl H H 2,3,5-Me₃, 6-CH(SEt)Me 0 0 2607 Cl H H2,3,5-Me₃, 6-COMe 0 0 2608 Cl H H 2,3,5-Me₃, 6-NO₂ 0 0 2609 Cl H H2,4-Cl₂, 3,5,6-Me₃ 0 0 2610 Cl H H 2,3,4,5,6-F₅ 0 0 2611 Cl H H2,3,4,5,6-Cl₅ 0 0 2612 Cl H H 2-Cl, 3,4,5,6-Me₄ 0 0 2613 Cl H H 2-Br,3,4,5,6-Me₄ 0 0 2614 Cl H H 2,3,4,5,6-Me₅ 0 0 2615 Cl H H 2,3,4,4,6-Et 00 2616 Cl H H 2,3,4,5-Me₄, 6-iPr 0 0 2617 Cl H H 2,3,4,5-Me₄, 6-cPr 0 02618 Cl H COEt 2-Cl 0 0 2619 Cl H COEt 2-Br 0 0 2620 Cl H COEt 2-I 0 02621 Cl H COEt 2-cBu 0 0 2622 Cl H COEt 2-cPr, 5-Me 0 0 2623 Cl H COEt2-OMe, 5-Me 0 0 2624 Cl H COEt 2-F, 6-iPr 0 0 2625 Cl H COEt 2-Cl, 6-cPr0 0 2626 Cl H COEt 2-Br, 6-Me 0 0 2627 Cl H COEt 2-I, 6-Me 0 0 2628 Cl HCOEt 2-Me, 6-Et 0 0 2629 Cl H COEt 2,6-cPr₂ 0 0 2630 Cl H COEt 2-cPr,3,5-Me₂ 0 0 2631 Cl H COEt 2-cPr, 3,6-Me₂ 0 0 2632 Cl H COiPr 2-Cl 0 02633 Cl H COiPr 2-Br 0 0 2634 Cl H COiPr 2-I 0 0 2635 Cl H COiPr 2-cBu 00 2636 Cl H COiPr 2-cPr, 5-Me 0 0 2637 Cl H COiPr 2-OMe, 5-Me 0 0 2638Cl H COiPr 2-F, 6-iPr 0 0 2639 Cl H COiPr 2-Cl, 6-cPr 0 0 2640 Cl HCOiPr 2-Br, 6-Me 0 0 2641 Cl H COiPr 2-I, 6-Me 0 0 2642 Cl H COiPr 2-Me,6-Et 0 0 2643 Cl H COiPr 2,6-cPr₂ 0 0 2644 Cl H COiPr 2-cPr, 3,5-Me₂ 0 02645 Cl H COiPr 2-cPr, 3,6-Me₂ 0 0 2646 Cl H COneoPen 2-Cl 0 0 2647 Cl HCOneoPen 2-Br 0 0 2648 Cl H COneoPen 2-I 0 0 2649 Cl H COneoPen 2-Me 0 02650 Cl H COneoPen 2-iPr 0 0 2651 Cl H COneoPen 2-cPr 0 0 2652 Cl HCOneoPen 2-cBu 0 0 2653 Cl H COneoPen 2-CH₂CH₂CH₂-3 0 0 2654 Cl HCOneoPen 2-cPr, 5-Me 0 0 2655 Cl H COneoPen 2-OMe, 5-Me 0 0 2656 Cl HCOneoPen 2-F, 6-iPr 0 0 2657 Cl H COneoPen 2-Cl, 6-cPr 0 0 2658 Cl HCOneoPen 2-Br, 6-Me 0 0 2659 Cl H COneoPen 2-I, 6-Me 0 0 2660 Cl HCOneoPen 2,6-Me₂ 0 0 2661 Cl H COneoPen 2-Me, 6-Et 0 0 2662 Cl HCOneoPen 2-Me, 6-cPr 0 0 2663 Cl H COneoPen 2,6-cPr₂ 0 0 2664 Cl HCOneoPen 2-cPr, 3,5-Me₂ 0 0 2665 Cl H COneoPen 2-cPr, 3,6-Me₂ 0 0 2666Cl H CO(1-Ad) 2-Me 0 0 2667 Cl H CO(1-Ad) 2-iPr 0 0 2668 Cl H CO(1-Ad)2-cPr 0 0 2669 Cl H CO(1-Ad) 2-CH₂CH₂CH₂-3 0 0 2670 Cl H CO(1-Ad)2,6-Me₂ 0 0 2671 Cl H CO(1-Ad) 2-Me, 6-cPr 0 0 2672 Cl H COCMe═CH₂ 2-Me0 0 2673 Cl H COCMe═CH₂ 2-iPr 0 0 2674 Cl H COCMe═CH₂ 2-cPr 0 0 2675 ClH COCMe═CH₂ 2-CH₂CH₂CH₂-3 0 0 2676 Cl H COCMe═CH₂ 2,6-Me₂ 0 0 2677 Cl HCOCMe═CH₂ 2-Me, 6-cPr 0 0 2678 Cl H COCH═CMe₂ 2-Cl 0 0 2679 Cl HCOCH═CMe₂ 2-Br 0 0 2680 Cl H COCH═CMe₂ 2-I 0 0 2681 Cl H COCH═CMe₂ 2-cBu0 0 2682 Cl H COCH═CMe₂ 2-cPr, 5-Me 0 0 2683 Cl H COCH═CMe₂ 2-OMe, 5-Me0 0 2684 Cl H COCH═CMe₂ 2-F, 6-iPr 0 0 2685 Cl H COCH═CMe₂ 2-Cl, 6-cPr 00 2686 Cl H COCH═CMe₂ 2-Br, 6-Me 0 0 2687 Cl H COCH═CMe₂ 2-I, 6-Me 0 02688 Cl H COCH═CMe₂ 2-Me, 6-Et 0 0 2689 Cl H COCH═CMe₂ 2,6-cPr₂ 0 0 2690Cl H COCH═CMe₂ 2-cPr, 3,5-Me₂ 0 0 2691 Cl H COCH═CMe₂ 2-cPr, 3,6-Me₂ 0 02692 Cl H COCMe₂Br 2-Me 0 0 2693 Cl H COCMe₂Br 2-iPr 0 0 2694 Cl HCOCMe₂Br 2-cPr 0 0 2695 Cl H COCMe₂Br 2-CH₂CH₂CH₂-3 0 0 2696 Cl HCOCMe₂Br 2,6-Me₂ 0 0 2697 Cl H COCMe₂Br 2-Me, 6-cPr 0 0 2698 Cl HCOCMe₂CH₂Cl 2-Me 0 0 2699 Cl H COCMe₂CH₂Cl 2-iPr 0 0 2700 Cl HCOCMe₂CH₂Cl 2-cPr 0 0 2701 Cl H COCMe₂CH₂Cl 2-CH₂CH₂CH₂-3 0 0 2702 Cl HCOCMe₂CH₂Cl 2,6-Me₂ 0 0 2703 Cl H COCMe₂CH₂Cl 2-Me, 6-cPr 0 0 2704 Cl HCOCH₂CH₂CH₂CH₂Br 2-Me 0 0 2705 Cl H COCH₂CH₂CH₂CH₂Br 2-iPr 0 0 2706 Cl HCOCH₂CH₂CH₂CH₂Br 2-cPr 0 0 2707 Cl H COCH₂CH₂CH₂CH₂Br 2-CH₂CH₂CH₂-3 0 02708 Cl H COCH₂CH₂CH₂CH₂Br 2,6-Me₂ 0 0 2709 Cl H COCH₂CH₂CH₂CH₂Br 2-Me,6-cPr 0 0 2710 Cl H COCHMePh 2-Me 0 0 2711 Cl H COCHMePh 2-iPr 0 0 2712Cl H COCHMePh 2-cPr 0 0 2713 Cl H COCHMePh 2-CH₂CH₂CH₂-3 0 0 2714 Cl HCOCHMePh 2,6-Me₂ 0 0 2715 Cl H COCHMePh 2-Me, 6-cPr 0 0 2716 Cl H COCH₂(Ph-4-OMe) 2-Me 0 0 2717 Cl H COCH₂ (Ph-4-OMe) 2-iPr 0 0 2718 Cl H COCH₂(Ph-4-OMe) 2-cPr 0 0 2719 Cl H COCH₂ (Ph-4-OMe) 2-CH₂CH₂CH₂-3 0 0 2720Cl H COCH₂ (Ph-4-OMe) 2,6-Me₂ 0 0 2721 Cl H COCH₂ (Ph-4-OMe) 2-Me, 6-cPr0 0 2722 Cl H COCH₂CH₂CO₂Et 2-Me 0 0 2723 Cl H COCH₂CH₂CO₂Et 2-iPr 0 02724 Cl H COCH₂CH₂CO₂Et 2-cPr 0 0 2725 Cl H COCH₂CH₂CO₂Et 2-CH₂CH₂CH₂-30 0 2726 Cl H COCH₂CH₂CO₂Et 2,6-Me₂ 0 0 2727 Cl H COCH₂CH₂CO₂Et 2-Me,6-cPr 0 0 2728 Cl H CO(CH₂)₂CO₂Q⁶ 2-Me 0 0 2729 Cl H CO(CH₂)₂CO₂Q⁷ 2-iPr0 0 2730 Cl H CO(CH₂)₂CO₂Q⁸ 2-cPr 0 0 2731 Cl H CO(CH₂)₂CO₂Q⁹2-CH₂CH₂CH₂-3 0 0 2732 Cl H CO(CH₂)₂CO₂Q¹⁰ 2,6-Me₂ 0 0 2733 Cl HCO(CH₂)₂CO₂Q¹¹ 2-Me, 6-cPr 0 0 2734 Cl H CO(CH₂)₃CO₂Q⁵ 2-Me 0 0 2735 ClH CO(CH₂)₃CO₂Q⁵ 2-iPr 0 0 2736 Cl H CO(CH₂)₃CO₂Q⁵ 2-cPr 0 0 2737 Cl HCO(CH₂)₃CO₂Q⁵ 2-CH₂CH₂CH₂-3 0 0 2738 Cl H CO(CH₂)₃CO₂Q⁵ 2,6-Me₂ 0 0 2739Cl H CO(CH₂)₃CO₂Q⁵ 2-Me, 6-cPr 0 0 2740 Cl H CO(CH₂)₃CO₂Q¹² 2-Me, 6-cPr0 0 2741 Cl H CO(CH₂)₃CO₂Q¹³ 2-Me, 6-cPr 0 0 2742 Cl H CO(CH₂)₃CO₂Q¹⁴2-Me, 6-cPr 0 0 2743 Cl H CO(CH₂)₃CO₂Q¹⁵ 2-Me, 6-cPr 0 0 2744 Cl HCO(CH₂)₃CO₂Q¹⁶ 2-Me, 6-cPr 0 0 2745 Cl H CO(CH₂)₃CO₂Q¹⁷ 2-Me, 6-cPr 0 02746 Cl H CO(CH₂)₃CO₂Q¹¹ 2-Me, 6-cPr 0 0 2747 Cl H COCH₂OMe 2-Me 0 02748 Cl H COCH₂OMe 2-iPr 0 0 2749 Cl H COCH₂OMe 2-cPr 0 0 2750 Cl HCOCH₂OMe 2-CH₂CH₂CH₂-3 0 0 2751 Cl H COCH₂OMe 2,6-Me₂ 0 0 2752 Cl HCOCH₂OMe 2-Me, 6-cPr 0 0 2753 Cl H COCH₂OPh 2-Me 0 0 2754 Cl H COCH₂OPh2-iPr 0 0 2755 Cl H COCH₂OPh 2-cPr 0 0 2756 Cl H COCH₂OPh 2-CH₂CH₂CH₂-30 0 2757 Cl H COCH₂OPh 2,6-Me₂ 0 0 2758 Cl H COCH₂OPh 2-Me, 6-cPr 0 02759 Cl H COCH(Me)OPh 2-Me 0 0 2760 Cl H COCH(Me)OPh 2-iPr 0 0 2761 Cl HCOCH(Me)OPh 2-cPr 0 0 2762 Cl H COCH(Me)OPh 2-CH₂CH₂CH₂-3 0 0 2763 Cl HCOCH(Me)OPh 2,6-Me₂ 0 0 2764 Cl H COCH(Me)OPh 2-Me, 6-cPr 0 0 2765 Cl HCOCH(OMe)Ph 2-Me 0 0 2766 Cl H COCH(OMe)Ph 2-iPr 0 0 2767 Cl HCOCH(OMe)Ph 2-cPr 0 0 2768 Cl H COCH(OMe)Ph 2-CH₂CH₂CH₂-3 0 0 2769 Cl HCOCH(OMe)Ph 2,6-Me₂ 0 0 2770 Cl H COCH(OMe)Ph 2-Me, 6-cPr 0 0 2771 Cl HCOCH₂CH₂SMe 2-Me 0 0 2772 Cl H COCH₂CH₂SMe 2-iPr 0 0 2773 Cl HCOCH₂CH₂SMe 2-cPr 0 0 2774 Cl H COCH₂CH₂SMe 2-CH₂CH₂CH₂-3 0 0 2775 Cl HCOCH₂CH₂SMe 2,6-Me₂ 0 0 2776 Cl H COCH₂CH₂SMe 2-Me, 6-cPr 0 0 2777 Cl HCOCO(2-Thi) 2-Me 0 0 2778 Cl H COCO(2-Thi) 2-iPr 0 0 2779 Cl HCOCO(2-Thi) 2-cPr 0 0 2780 Cl H COCO(2-Thi) 2-CH₂CH₂CH₂-3 0 0 2781 Cl HCOCO(2-Thi) 2,6-Me₂ 0 0 2782 Cl H COCO(2-Thi) 2-Me, 6-cPr 0 0 2783 Cl HCO(Ph-2-F) 2-Me 0 0 2784 Cl H CO(Ph-2-F) 2-iPr 0 0 2785 Cl H CO(Ph-2-F)2-cPr 0 0 2786 Cl H CO(Ph-2-F) 2-CH₂CH₂CH₂-3 0 0 2787 Cl H CO(Ph-2-F)2,6-Me₂ 0 0 2788 Cl H CO(Ph-2-F) 2-Me, 6-cPr 0 0 2789 Cl H CO(Ph-2-Br)2-Cl 0 0 2790 Cl H CO(Ph-2-Br) 2-Br 0 0 2791 Cl H CO(Ph-2-Br) 2-I 0 02792 Cl H CO(Ph-2-Br) 2-Me 0 0 2793 Cl H CO(Ph-2-Br) 2-iPr 0 0 2794 Cl HCO(Ph-2-Br) 2-cPr 0 0 2795 Cl H CO(Ph-2-Br) 2-cBu 0 0 2796 Cl HCO(Ph-2-Br) 2-CH₂CH₂CH₂-3 0 0 2797 Cl H CO(Ph-2-Br) 2-cPr, 5-Me 0 0 2798Cl H CO(Ph-2-Br) 2-OMe, 5-Me 0 0 2799 Cl H CO(Ph-2-Br) 2-F, 6-iPr 0 02800 Cl H CO(Ph-2-Br) 2-Cl, 6-cPr 0 0 2801 Cl H CO(Ph-2-Br) 2-Br, 6-Me 00 2802 Cl H CO(Ph-2-Br) 2-I, 6-Me 0 0 2803 Cl H CO(Ph-2-Br) 2,6-Me₂ 0 02804 Cl H CO(Ph-2-Br) 2-Me, 6-Et 0 0 2805 Cl H CO(Ph-2-Br) 2-Me, 6-cPr 00 2806 Cl H CO(Ph-2-Br) 2,6-cPr₂ 0 0 2807 Cl H CO(Ph-2-Br) 2-cPr,3,5-Me₂ 0 0 2808 Cl H CO(Ph-2-Br) 2-cPr, 3,6-Me₂ 0 0 2809 Cl HCO(Ph-2-I) 2-Me 0 0 2810 Cl H CO(Ph-2-I) 2-iPr 0 0 2811 Cl H CO(Ph-2-I)2-cPr 0 0 2812 Cl H CO(Ph-2-I) 2-CH₂CH₂CH₂-3 0 0 2813 Cl H CO(Ph-2-I)2,6-Me₂ 0 0 2814 Cl H CO(Ph-2-I) 2-Me, 6-cPr 0 0 2815 Cl H CO(Ph-2-CF₃)2-Me 0 0 2816 Cl H CO(Ph-2-CF₃) 2-iPr 0 0 2817 Cl H CO(Ph-2-CF₃) 2-cPr 00 2818 Cl H CO(Ph-2-CF₃) 2-CH₂CH₂CH₂-3 0 0 2819 Cl H CO(Ph-2-CF₃)2,6-Me₂ 0 0 2820 Cl H CO(Ph-2-CF₃) 2-Me, 6-cPr 0 0 2821 Cl HCO(Ph-2-CH₂Ph) 2-Me 0 0 2822 Cl H CO(Ph-2-CH₂Ph) 2-iPr 0 0 2823 Cl HCO(Ph-2-CH₂Ph) 2-cPr 0 0 2824 Cl H CO(Ph-2-CH₂Ph) 2-CH₂CH₂CH₂-3 0 0 2825Cl H CO(Ph-2-CH₂Ph) 2,6-Me₂ 0 0 2826 Cl H CO(Ph-2-CH₂Ph) 2-Me, 6-cPr 0 02827 Cl H CO(Ph-2-CO₂Q⁶) 2-Me 0 0 2828 Cl H CO(Ph-2-CO₂Q¹²) 2-Me 0 02829 Cl H CO(Ph-2-CO₂Q¹³) 2-Me 0 0 2830 Cl H CO(Ph-2-CO₂Q¹⁴) 2-Me 0 02831 Cl H CO(Ph-2-CO₂Q¹⁵) 2-Me 0 0 2832 Cl H CO(Ph-2-CO₂Q¹⁶) 2-Me 0 02833 Cl H CO(Ph-2-CO₂Q¹⁷) 2-Me 0 0 2834 Cl H CO(Ph-2-CO₂Q⁷) 2-iPr 0 02835 Cl H CO(Ph-2-CO₂Q⁸) 2-cPr 0 0 2836 Cl H CO(Ph-2-CO₂Q⁹)2-CH₂CH₂CH₂-3 0 0 2837 Cl H CO(Ph-2-CO₂Q¹⁰) 2,6-Me₂ 0 0 2838 Cl HCO(Ph-2-CO₂Q¹¹) 2-Me, 6-cPr 0 0 2839 Cl H CO(Ph-2-CO₂Q¹²) 2-Me, 6-cPr 00 2840 Cl H CO(Ph-2-CO₂Q¹³) 2-Me, 6-cPr 0 0 2841 Cl H CO(Ph-2-CO₂Q¹⁴)2-Me, 6-cPr 0 0 2842 Cl H CO(Ph-2-CO₂Q¹⁵) 2-Me, 6-cPr 0 0 2843 Cl HCO(Ph-2-CO₂Q¹⁶) 2-Me, 6-cPr 0 0 2844 Cl H CO(Ph-2-CO₂Q¹⁷) 2-Me, 6-cPr 00 2845 Cl H CO(Ph-2-NO₂) 2-Me 0 0 2846 Cl H CO(Ph-2-NO₂) 2-iPr 0 0 2847Cl H CO(Ph-2-NO₂) 2-cPr 0 0 2848 Cl H CO(Ph-2-NO₂) 2-CH₂CH₂CH₂-3 0 02849 Cl H CO(Ph-2-NO₂) 2,6-Me₂ 0 0 2850 Cl H CO(Ph-2-NO₂) 2-Me, 6-cPr 00 2851 Cl H CO(Ph-2-OPh) 2-Me 0 0 2852 Cl H CO(Ph-2-OPh) 2-iPr 0 0 2853Cl H CO(Ph-2-OPh) 2-cPr 0 0 2854 Cl H CO(Ph-2-OPh) 2-CH₂CH₂CH₂-3 0 02855 Cl H CO(Ph-2-OPh) 2,6-Me₂ 0 0 2856 Cl H CO(Ph-2-OPh) 2-Me, 6-cPr 00 2857 Cl H CO(Ph-3-F) 2-Me 0 0 2858 Cl H CO(Ph-3-F) 2-iPr 0 0 2859 Cl HCO(Ph-3-F) 2-cPr 0 0 2860 Cl H CO(Ph-3-F) 2-CH₂CH₂CH₂-3 0 0 2861 Cl HCO(Ph-3-F) 2,6-Me₂ 0 0 2862 Cl H CO(Ph-3-F) 2-Me, 6-cPr 0 0 2863 Cl HCO(Ph-3-Cl) 2-Me 0 0 2864 Cl H CO(Ph-3-Cl) 2-iPr 0 0 2865 Cl HCO(Ph-3-Cl) 2-cPr 0 0 2866 Cl H CO(Ph-3-Cl) 2-CH₂CH₂CH₂-3 0 0 2867 Cl HCO(Ph-3-Cl) 2,6-Me₂ 0 0 2868 Cl H CO(Ph-3-Cl) 2-Me, 6-cPr 0 0 2869 Cl HCO(Ph-3-Br) 2-Me 0 0 2870 Cl H CO(Ph-3-Br) 2-iPr 0 0 2871 Cl HCO(Ph-3-Br) 2-cPr 0 0 2872 Cl H CO(Ph-3-Br) 2-CH₂CH₂CH₂-3 0 0 2873 Cl HCO(Ph-3-Br) 2,6-Me₂ 0 0 2874 Cl H CO(Ph-3-Br) 2-Me, 6-cPr 0 0 2875 Cl HCO(Ph-3-I) 2-Me 0 0 2876 Cl H CO(Ph-3-I) 2-iPr 0 0 2877 Cl H CO(Ph-3-I)2-cPr 0 0 2878 Cl H CO(Ph-3-I) 2-CH₂CH₂CH₂-3 0 0 2879 Cl H CO(Ph-3-I)2,6-Me₂ 0 0 2880 Cl H CO(Ph-3-I) 2-Me, 6-cPr 0 0 2881 Cl H CO(Ph-3-Me)2-Cl 0 0 2882 Cl H CO(Ph-3-Me) 2-Br 0 0 2883 Cl H CO(Ph-3-Me) 2-I 0 02884 Cl H CO(Ph-3-Me) 2-cBu 0 0 2885 Cl H CO(Ph-3--Me) 2-cPr, 5-Me 0 02886 Cl H CO(Ph-3-Me) 2-OMe, 5-Me 0 0 2887 Cl H CO(Ph-3-Me) 2-F, 6-iPr 00 2888 Cl H CO(Ph-3-Me) 2-Cl, 6-cPr 0 0 2889 Cl H CO(Ph-3-Me) 2-Br, 6-Me0 0 2890 Cl H CO(Ph-3-Me) 2-I, 6-Me 0 0 2891 Cl H CO(Ph-3-Me) 2-Me, 6-Et0 0 2892 Cl H CO(Ph-3-Me) 2,6-cPr₂ 0 0 2893 Cl H CO(Ph-3-Me) 2-cPr,3,5-Me₂ 0 0 2894 Cl H CO(Ph-3-Me) 2-cPr, 3,6-Me₂ 0 0 2895 Cl HCO(Ph-3-CF₃) 2-Me 0 0 2896 Cl H CO(Ph-3-CF₃) 2-iPr 0 0 2897 Cl HCO(Ph-3-CF₃) 2-cPr 0 0 2898 Cl H CO(Ph-3-CF₃) 2-CH₂CH₂CH₂-3 0 0 2899 ClH CO(Ph-3-CF₃) 2,6-Me₂ 0 0 2900 Cl H CO(Ph-3-CF₃) 2-Me, 6-cPr 0 0 2901Cl H CO(Ph-3-CO₂Q⁶) 2-Me 0 0 2902 Cl H CO(Ph-3-CO₂Q⁷) 2-iPr 0 0 2903 ClH CO(Ph-3-CO₂Q⁸) 2-cPr 0 0 2904 Cl H CO(Ph-3-CO₂Q⁹) 2-CH₂CH₂CH₂-3 0 02905 Cl H CO(Ph-3-CO₂Q¹⁰) 2,6-Me₂ 0 0 2906 Cl H CO(Ph-3-CO₂Q¹¹) 2-Me,6-cPr 0 0 2907 Cl H CO(Ph-3-CO₂Q¹²) 2-Me, 6-cPr 0 0 2908 Cl HCO(Ph-3-CO₂Q¹³) 2-Me, 6-cPr 0 0 2909 Cl H CO(Ph-3-CO₂Q¹⁴) 2-Me, 6-cPr 00 2910 Cl H CO(Ph-3-CO₂Q¹⁵) 2-Me, 6-cPr 0 0 2911 Cl H CO(Ph-3-CO₂Q¹⁶)2-Me, 6-cPr 0 0 2912 Cl H CO(Ph-3-CO₂Q¹⁷) 2-Me., 6-cPr 0 0 2913 Cl HCO(Ph-3-NO₂) 2-Me 0 0 2914 Cl H CO(Ph-3-NO₂) 2-iPr 0 0 2915 Cl HCO(Ph-3-NO₂) 2-cPr 0 0 2916 Cl H CO(Ph-3-NO₂) 2-CH₂CH₂CH₂-3 0 0 2917 ClH CO(Ph-3-NO₂) 2,6-Me₂ 0 0 2918 Cl H CO(Ph-3-NO₂) 2-Me, 6-cPr 0 0 2919Cl H CO(Ph-3-OPh) 2-Me 0 0 2920 Cl H CO(Ph-3-OPh) 2-iPr 0 0 2921 Cl HCO(Ph-3-OPh) 2-cPr 0 0 2922 Cl H CO(Ph-3-OPh) 2-CH₂CH₂CH₂-3 0 0 2923 ClH CO(Ph-3-OPh) 2,6-Me₂ 0 0 2924 Cl H CO(Ph-3-OPh) 2-Me, 6-cPr 0 0 2925Cl H CO(Ph-4-F) 2-Me 0 0 2926 Cl H CO(Ph-4-F) 2-iPr 0 0 2927 Cl HCO(Ph-4-F) 2-cPr 0 0 2928 Cl H CO(Ph-4-F) 2-CH₂CH₂CH₂-3 0 0 2929 Cl HCO(Ph-4-F) 2,6-Me₂ 0 0 2930 Cl H CO(Ph-4-F) 2-Me, 6-cPr 0 0 2931 Cl HCO(Ph-4-Br) 2-Cl 0 0 2932 Cl H CO(Ph-4-Br) 2-Br 0 0 2933 Cl HCO(Ph-4-Br) 2-I 0 0 2934 Cl H CO(Ph-4-Br) 2-cBu 0 0 2935 Cl HCO(Ph-4-Br) 2-cPr, 5-Me 0 0 2936 Cl H CO(Ph-4-Br) 2-OMe, 5-Me 0 0 2937Cl H CO(Ph-4-Br) 2-F, 6-iPr 0 0 2938 Cl H CO(Ph-4-Br) 2-Cl, 6-cPr 0 02939 Cl H CO(Ph-4-Br) 2-Br, 6-Me 0 0 2940 Cl H CO(Ph-4-Br) 2-I, 6-Me 0 02941 Cl H CO(Ph-4-Br) 2-Me, 6-Et 0 0 2942 Cl H CO(Ph-4-Br) 2,6-cPr₂ 0 02943 Cl H CO(Ph-4-Br) 2-cPr, 3,5-Me₂ 0 0 2944 Cl H CO(Ph-4-Br) 2-cPr,3,6-Me₂ 0 0 2945 Cl H CO(Ph-4-Et) 2-Cl 0 0 2946 Cl H CO(Ph-4-Et) 2-Br 00 2947 Cl H CO(Ph-4-Et) 2-I 0 0 2948 Cl H CO(Ph-4-Et) 2-Me 0 0 2949 Cl HCO(Ph-4-Et) 2-iPr 0 0 2950 Cl H CO(Ph-4-Et) 2-cPr 0 0 2951 Cl HCO(Ph-4-Et) 2-cBu 0 0 2952 Cl H CO(Ph-4-Et) 2-CH₂CH₂CH₂-3 0 0 2953 Cl HCO(Ph-4-Et) 2-cPr, 5-Me 0 0 2954 Cl H CO(Ph-4-Et) 2-OMe, 5-Me 0 0 2955Cl H CO(Ph-4-Et) 2-F, 6-iPr 0 0 2956 Cl H CO(Ph-4-Et) 2-Cl, 6-cPr 0 02957 Cl H CO(Ph-4-Et) 2-Br, 6-Me 0 0 2958 Cl H CO(Ph-4-Et) 2-I, 6-Me 0 02959 Cl H CO(Ph-4-Et) 2,6-Me₂ 0 0 2960 Cl H CO(Ph-4-Et) 2-Me, 6-Et 0 02961 Cl H CO(Ph-4-Et) 2-Me, 6-cPr 0 0 2962 Cl H CO(Ph-4-Et) 2,6-cPr₂ 0 02963 Cl H CO(Ph-4-Et) 2-cPr, 3,5-Me₂ 0 0 2964 Cl H CO(Ph-4-Et) 2-cPr,3,6-Me₂ 0 0 2965 Cl H CO(Ph-4-Pr) 2-Me 0 0 2966 Cl H CO(Ph-4-Pr) 2-iPr 00 2967 Cl H CO(Ph-4-Pr) 2-cPr 0 0 2968 Cl H CO(Ph-4-Pr) 2-CH₂CH₂CH₂-3 00 2969 Cl H CO(Ph-4-Pr) 2,6-Me₂ 0 0 2970 Cl H CO(Ph-4-Pr) 2-Me, 6-cPr 00 2971 Cl H CO(Ph-4-iPr) 2-Me 0 0 2972 Cl H CO(Ph-4-iPr) 2-iPr 0 0 2973Cl H CO(Ph-4-iPr) 2-cPr 0 0 2974 Cl H CO(Ph-4-iPr) 2-CH₂CH₂CH₂-3 0 02975 Cl H CO(Ph-4-iPr) 2,6-Me₂ 0 0 2976 Cl H CO(Ph-4-iPr) 2-Me, 6-cPr 00 2977 Cl H CO(Ph-4-Bu) 2-Me 0 0 2978 Cl H CO(Ph-4-Bu) 2-iPr 0 0 2979 ClH CO(Ph-4-Bu) 2-cPr 0 0 2980 Cl H CO(Ph-4-Bu) 2-CH₂CH₂CH₂-3 0 0 2981 ClH CO(Ph-4-Bu) 2,6-Me₂ 0 0 2982 Cl H CO(Ph-4-Bu) 2-Me, 6-cPr 0 0 2983 ClH CO(Ph-4-CF₃) 2-Me 0 0 2984 Cl H CO(Ph-4-CF₃) 2-iPr 0 0 2985 Cl HCO(Ph-4-CF₃) 2-cPr 0 0 2986 Cl H CO(Ph-4-CF₃) 2-CH₂CH₂CH₂-3 0 0 2987 ClH CO(Ph-4-CF₃) 2,6-Me₂ 0 0 2988 Cl H CO(Ph-4-CF₃) 2-Me, 6-cPr 0 0 2989Cl H CO(Ph-4-CN) 2-Me 0 0 2990 Cl H CO(Ph-4-CN) 2-iPr 0 0 2991 Cl HCO(Ph-4-CN) 2-cPr 0 0 2992 Cl H CO(Ph-4-CN) 2-CH₂CH₂CH₂-3 0 0 2993 Cl HCO(Ph-4-CN) 2,6-Me₂ 0 0 2994 Cl H CO(Ph-4-CN) 2-Me, 6-cPr 0 0 2995 Cl HCO(Ph-4-CO₂Q⁵) 2-Cl, 6-cPr 0 0 2996 Cl H CO(Ph-4-CO₂Q⁶) 2-Me 0 0 2997 ClH CO(Ph-4-CO₂Q⁷) 2-iPr 0 0 2998 Cl H CO(Ph-4-CO₂Q⁸) 2-cPr 0 0 2999 Cl HCO(Ph-4-CO₂Q⁹) 2-CH₂CH₂CH₂-3 0 0 3000 Cl H CO(Ph-4-CO₂Q¹⁰) 2,6-Me₂ 0 03001 Cl H CO(Ph-4-CO₂Q¹¹) 2-Me, 6-cPr 0 0 3002 Cl H CO(Ph-4-CO₂Q¹²)2-Me, 6-cPr 0 0 3003 Cl H CO(Ph-4-CO₂Q¹³) 2-Me, 6-cPr 0 0 3004 Cl HCO(Ph-4-CO₂Q¹⁴) 2-Me, 6-cPr 0 0 3005 Cl H CO(Ph-4-CO₂Q¹⁵) 2-Me, 6-cPr 00 3006 Cl H CO(Ph-4-CO₂Q¹⁶) 2-Me, 6-cPr 0 0 3007 Cl H CO(Ph-4-CO₂Q¹⁷)2-Me, 6-cPr 0 0 3008 Cl H CO(Ph-2-SO₂OQ⁵) 2-Me, 6-cPr 0 0 3009 Cl HCO(Ph-3-SO₂OQ⁵) 2-Me, 6-cPr 0 0 3010 Cl H CO(Ph-4-SO₂OQ⁵) 2-Me, 6-cPr 00 3011 Cl H CO(Ph-4-Ph) 2-Me 0 0 3012 Cl H CO(Ph-4-Ph) 2-iPr 0 0 3013 ClH CO(Ph-4-Ph) 2-cPr 0 0 3014 Cl H CO(Ph-4-Ph) 2-CH₂CH₂CH₂-3 0 0 3015 ClH CO(Ph-4-Ph) 2,6-Me₂ 0 0 3016 Cl H CO(Ph-4-Ph) 2-Me, 6-cPr 0 0 3017 ClH CO(Ph-4-OCF₃) 2-Me 0 0 3018 Cl H CO(Ph-4-OCF₃) 2-iPr 0 0 3019 Cl HCO(Ph-4-OCF₃) 2-cPr 0 0 3020 Cl H CO(Ph-4-OCF₃) 2-CH₂CH₂CH₂-3 0 0 3021Cl H CO(Ph-4-OCF₃) 2,6-Me₂ 0 0 3022 Cl H CO(Ph-4-OCF₃) 2-Me, 6-cPr 0 03023 Cl H CO(Ph-4-OCH₂Ph) 2-Me 0 0 3024 Cl H CO(Ph-4-OCH₂Ph) 2-iPr 0 03025 Cl H CO(Ph-4-OCH₂Ph) 2-cPr 0 0 3026 Cl H CO(Ph-4-OCH₂Ph)2-CH₂CH₂CH₂-3 0 0 3027 Cl H CO(Ph-4-OCH₂Ph) 2,6-Me₂ 0 0 3028 Cl HCO(Ph-4-OCH₂Ph) 2-Me, 6-cPr 0 0 3029 Cl H CO(Ph-2,3-F₂) 2-Me 0 0 3030 ClH CO(Ph-2,3-F₂) 2-iPr 0 0 3031 Cl H CO(Ph-2,3-F₂) 2-cPr 0 0 3032 Cl HCO(Ph-2,3-F₂) 2-CH₂CH₂CH₂-3 0 0 3033 Cl H CO(Ph-2,3-F₂) 2,6-Me₂ 0 0 3034Cl H CO(Ph-2,3-F₂) 2-Me, 6-cPr 0 0 3035 Cl H CO(Ph-2-F-3-CF₃) 2-Me 0 03036 Cl H CO(Ph-2-F-3-CF₃) 2-iPr 0 0 3037 Cl H CO(Ph-2-F-3-CF₃) 2-cPr 00 3038 Cl H CO(Ph-2-F-3-CF₃) 2-CH₂CH₂CH₂-3 0 0 3039 Cl HCO(Ph-2-F-3-CF₃) 2,6-Me₂ 0 0 3040 Cl H CO(Ph-2-F-3-CF₃) 2-Me, 6-cPr 0 03041 Cl H CO(Ph-2,3-Me₂) 2-Me 0 0 3042 Cl H CO(Ph-2,3-Me₂) 2-iPr 0 03043 Cl H CO(Ph-2,3-Me₂) 2-cPr 0 0 3044 Cl H CO(Ph-2,3-Me₂)2-CH₂CH₂CH₂-3 0 0 3045 Cl H CO(Ph-2,3-Me₂) 2,6-Me₂ 0 0 3046 Cl HCO(Ph-2,3-Me₂) 2-Me, 6-cPr 0 0 3047 Cl H CO(Ph-2-Me-3-Cl) 2-Me 0 0 3048Cl H CO(Ph-2-Me-3-Cl) 2-iPr 0 0 3049 Cl H CO(Ph-2-Me-3-Cl) 2-cPr 0 03050 Cl H CO(Ph-2-Me-3-Cl) 2-CH₂CH₂CH₂-3 0 0 3051 Cl H CO(Ph-2-Me-3-Cl)2,6-Me₂ 0 0 3052 Cl H CO(Ph-2-Me-3-Cl) 2-Me, 6-cPr 0 0 3053 Cl HCO(Ph-2,4-F₂) 2-Me 0 0 3054 Cl H CO(Ph-2,4-F₂) 2-iPr 0 0 3055 Cl HCO(Ph-2,4-F₂) 2-cPr 0 0 3056 Cl H CO(Ph-2,4-F₂) 2-CH₂CH₂CH₂-3 0 0 3057Cl H CO(Ph-2,4-F₂) 2,6-Me₂ 0 0 3058 Cl H CO(Ph-2,4-F₂) 2-Me, 6-cPr 0 03059 Cl H CO(Ph-2-F-4-Cl) 2-Me 0 0 3060 Cl H CO(Ph-2-F-4-Cl) 2-iPr 0 03061 Cl H CO(Ph-2-F-4-Cl) 2-cPr 0 0 3062 Cl H CO(Ph-2-F-4-Cl)2-CH₂CH₂CH₂-3 0 0 3063 Cl H CO(Ph-2-F-4-Cl) 2,6-Me₂ 0 0 3064 Cl HCO(Ph-2-F-4-Cl) 2-Me, 6-cPr 0 0 3065 Cl H CO(Ph-2-F-4-CF₃) 2-Me 0 0 3066Cl H CO(Ph-2-F-4-CF₃) 2-iPr 0 0 3067 Cl H CO(Ph-2-F-4-CF₃) 2-cPr 0 03068 Cl H CO(Ph-2-F-4-CF₃) 2-CH₂CH₂CH₂-3 0 0 3069 Cl H CO(Ph-2-F-4-CF₃)2,6-Me₂ 0 0 3070 Cl H CO(Ph-2-F-4-CF₃) 2-Me, 6-cPr 0 0 3071 Cl HCO(Ph-2-Cl-4-F) 2-Me 0 0 3072 Cl H CO(Ph-2-Cl-4-F) 2-iPr 0 0 3073 Cl HCO(Ph-2-Cl-4-F) 2-cPr 0 0 3074 Cl H CO(Ph-2-Cl-4-F) 2-CH₂CH₂CH₂-3 0 03075 Cl H CO(Ph-2-Cl-4-F) 2,6-Me₂ 0 0 3076 Cl H CO(Ph-2-Cl-4-F) 2-Me,6-cPr 0 0 3077 Cl H CO(Ph-2-Cl-4-Br) 2-Me 0 0 3078 Cl H CO(Ph-2-Cl-4-Br)2-iPr 0 0 3079 Cl H CO(Ph-2-Cl-4-Br) 2-cPr 0 0 3080 Cl HCO(Ph-2-Cl-4-Br) 2-CH₂CH₂CH₂-3 0 0 3081 Cl H CO(Ph-2-Cl-4-Br) 2,6-Me₂ 00 3082 Cl H CO(Ph-2-Cl-4-Br) 2-Me, 6-cPr 0 0 3083 Cl H CO(Ph-2-Me-4-Br)2-Me 0 0 3084 Cl H CO(Ph-2-Me-4-Br) 2-iPr 0 0 3085 Cl H CO(Ph-2-Me-4-Br)2-cPr 0 0 3086 Cl H CO(Ph-2-Me-4-Br) 2-CH₂CH₂CH₂-3 0 0 3087 Cl HCO(Ph-2-Me-4-Br) 2,6-Me₂ 0 0 3088 Cl H CO(Ph-2-Me-4-Br) 2-Me, 6-cPr 0 03089 Cl H CO(Ph-2,4-Me₂) 2-Me 0 0 3090 Cl H CO(Ph-2,4-Me₂) 2-iPr 0 03091 Cl H CO(Ph-2,4-Me₂) 2-cPr 0 0 3092 Cl H CO(Ph-2,4-Me₂)2-CH₂CH₂CH₂-3 0 0 3093 Cl H CO(Ph-2,4-Me₂) 2,6-Me₂ 0 0 3094 Cl HCO(Ph-2,4-Me₂) 2-Me, 6-cPr 0 0 3095 Cl H CO(Ph-2,5-Cl₂) 2-Me 0 0 3096 ClH CO(Ph-2,5-Cl₂) 2-iPr 0 0 3097 Cl H CO(Ph-2,5-Cl₂) 2-cPr 0 0 3098 Cl HCO(Ph-2,5-Cl₂) 2-CH₂CH₂CH₂-3 0 0 3099 Cl H CO(Ph-2,5-Cl₂) 2,6-Me₂ 0 03100 Cl H CO(Ph-2,5-Cl₂) 2-Me, 6-cPr 0 0 3101 Cl H CO(Ph-2-Cl-5-Br) 2-Me0 0 3102 Cl H CO(Ph-2-Cl-5-Br) 2-iPr 0 0 3103 Cl H CO(Ph-2-Cl-5-Br)2-cPr 0 0 3104 Cl H CO(Ph-2-Cl-5-Br) 2-CH₂CH₂CH₂-3 0 0 3105 Cl HCO(Ph-2-Cl-5-Br) 2,6-Me₂ 0 0 3106 Cl H CO(Ph-2-Cl-5-Br) 2-Me, 6-cPr 0 03107 Cl H CO(Ph-2-Br-5-OMe) 2-Me 0 0 3108 Cl H CO(Ph-2-Br-5-OMe) 2-iPr 00 3109 Cl H CO(Ph-2-Br-5-OMe) 2-cPr 0 0 3110 Cl H CO(Ph-2-Br-5-OMe)2-CH₂CH₂CH₂-3 0 0 3111 Cl H CO(Ph-2-Br-5-OMe) 2,6-Me₂ 0 0 3112 Cl HCO(Ph-2-Br-5-OMe) 2-Me, 6-cPr 0 0 3113 Cl H CO(Ph-2,5-Me₂) 2-Cl 0 0 3114Cl H CO(Ph-2,5-Me₂) 2-Br 0 0 3115 Cl H CO(Ph-2,5-Me₂) 2-I 0 0 3116 Cl HCO(Ph-2,5-Me₂) 2-Me 0 0 3117 Cl H CO(Ph-2,5-Me₂) 2-iPr 0 0 3118 Cl HCO(Ph-2,5-Me₂) 2-cPr 0 0 3119 Cl H CO(Ph-2,5-Me₂) 2-cBu 0 0 3120 Cl HCO(Ph-2,5-Me₂) 2-CH₂CH₂CH₂-3 0 0 3121 Cl H CO(Ph-2,5-Me₂) 2-cPr, 5-Me 00 3122 Cl H CO(Ph-2,5-Me₂) 2-OMe, 5-Me 0 0 3123 Cl H CO(Ph-2,5-Me₂) 2-F,6-iPr 0 0 3124 Cl H CO(Ph-2,5-Me₂) 2-Cl, 6-cPr 0 0 3125 Cl HCO(Ph-2,5-Me₂) 2-Br, 6-Me 0 0 3126 Cl H CO(Ph-2,5-Me₂) 2-I, 6-Me 0 03127 Cl H CO(Ph-2,5-Me₂) 2,6-Me₂ 0 0 3128 Cl H CO(Ph-2,5-Me₂) 2-Me, 6-Et0 0 3129 Cl H CO(Ph-2,5-Me₂) 2-Me, 6-cPr 0 0 3130 Cl H CO(Ph-2,5-Me₂)2,6-cPr₂ 0 0 3131 Cl H CO(Ph-2,5-Me₂) 2-cPr, 3,5-Me₂ 0 0 3132 Cl HCO(Ph-2,5-Me₂) 2-cPr, 3,6-Me₂ 0 0 3133 Cl H CO(Ph-2,6-F₂) 2-Me 0 0 3134Cl H CO(Ph-2,6-F₂) 2-iPr 0 0 3135 Cl H CO(Ph-2,6-F₂) 2-cPr 0 0 3136 Cl HCO(Ph-2,6-F₂) 2-CH₂CH₂CH₂-3 0 0 3137 Cl H CO(Ph-2,6-F₂) 2,6-Me₂ 0 0 3138Cl H CO(Ph-2,6-F₂) 2-Me, 6-cPr 0 0 3139 Cl H CO(Ph-2-F-6-Cl) 2-Me 0 03140 Cl H CO(Ph-2-F-6-Cl) 2-iPr 0 0 3141 Cl H CO(Ph-2-F-6-Cl) 2-cPr 0 03142 Cl H CO(Ph-2-F-6-Cl) 2-CH₂CH₂CH₂-3 0 0 3143 Cl H CO(Ph-2-F-6-Cl)2,6-Me₂ 0 0 3144 Cl H CO(Ph-2-F-6-Cl) 2-Me, 6-cPr 0 0 3145 Cl HCO(Ph-2,6-Cl₂) 2-Me 0 0 3146 Cl H CO(Ph-2,6-Cl₂) 2-iPr 0 0 3147 Cl HCO(Ph-2,6-Cl₂) 2-cPr 0 0 3148 Cl H CO(Ph-2,6-Cl₂) 2-CH₂CH₂CH₂-3 0 0 3149Cl H CO(Ph-2,6-Cl₂) 2,6-Me₂ 0 0 3150 Cl H CO(Ph-2,6-Cl₂) 2-Me, 6-cPr 0 03151 Cl H CO(Ph-2,6-Me₂) 2-Me 0 0 3152 Cl H CO(Ph-2,6-Me₂) 2-iPr 0 03153 Cl H CO(Ph-2,6-Me₂) 2-cPr 0 0 3154 Cl H CO(Ph-2,6-Me₂)2-CH₂CH₂CH₂-3 0 0 3155 Cl H CO(Ph-2,6-Me₂) 2,6-Me₂ 0 0 3156 Cl HCO(Ph-2,6-Me₂) 2-Me, 6-cPr 0 0 3157 Cl H CO{Ph-2,6-(OMe)₂} 2-Me 0 0 3158Cl H CO{Ph-2,6-(OMe)₂} 2-iPr 0 0 3159 Cl H CO{Ph-2,6-(OMe)₂} 2-cPr 0 03160 Cl H CO{Ph-2,6-(OMe)₂} 2-CH₂CH₂CH₂-3 0 0 3161 Cl HCO{Ph-2,6-(OMe)₂} 2,6-Me₂ 0 0 3162 Cl H CO{Ph-2,6-(OMe)₂} 2-Me, 6-cPr 00 3163 Cl H CO(Ph-3,4-F₂) 2-Me 0 0 3164 Cl H CO(Ph-3,4-F₂) 2-iPr 0 03165 Cl H CO(Ph-3,4-F₂) 2-cPr 0 0 3166 Cl H CO(Ph-3,4-F₂) 2-CH₂CH₂CH₂-30 0 3167 Cl H CO(Ph-3,4-F₂) 2,6-Me₂ 0 0 3168 Cl H CO(Ph-3,4-F₂) 2-Me,6-cPr 0 0 3169 Cl H CO(Ph-3-F-4-Me) 2-Cl 0 0 3170 Cl H CO(Ph-3-F-4-Me)2-Br 0 0 3171 Cl H CO(Ph-3-F-4-Me) 2-I 0 0 3172 Cl H CO(Ph-3-F-4-Me)2-Me 0 0 3173 Cl H CO(Ph-3-F-4-Me) 2-iPr 0 0 3174 Cl H CO(Ph-3-F-4-Me)2-cPr 0 0 3175 Cl H CO(Ph-3-F-4-Me) 2-cBu 0 0 3176 Cl H CO(Ph-3-F-4-Me)2-CH₂CH₂CH₂-3 0 0 3177 Cl H CO(Ph-3-F-4-Me) 2-cPr, 5-Me 0 0 3178 Cl HCO(Ph-3-F-4-Me) 2-OMe, 5-Me 0 0 3179 Cl H CO(Ph-3-F-4-Me) 2-F, 6-iPr 0 03180 Cl H CO(Ph-3-F-4-Me) 2-Cl, 6-cPr 0 0 3181 Cl H CO(Ph-3-F-4-Me)2-Br, 6-Me 0 0 3182 Cl H CO(Ph-3-F-4-Me) 2-I, 6-Me 0 0 3183 Cl HCO(Ph-3-F-4-Me) 2,6-Me₂ 0 0 3184 Cl H CO(Ph-3-F-4-Me) 2-Me, 6-Et 0 03185 Cl H CO(Ph-3-F-4-Me) 2-Me, 6-cPr 0 0 3186 Cl H CO(Ph-3-F-4-Me)2,6-cPr₂ 0 0 3187 Cl H CO(Ph-3-F-4-Me) 2-cPr, 3,5-Me₂ 0 0 3188 Cl HCO(Ph-3-F-4-Me) 2-cPr, 3,6-Me₂ 0 0 3189 Cl H CO(Ph-3,4-Cl₂) 2-Me 0 03190 Cl H CO(Ph-3,4-Cl₂) 2-iPr 0 0 3191 Cl H CO(Ph-3,4-Cl₂) 2-cPr 0 03192 Cl H CO(Ph-3,4-Cl₂) 2-CH₂CH₂CH₂-3 0 0 3193 Cl H CO(Ph-3,4-Cl₂)2,6-Me₂ 0 0 3194 Cl H CO(Ph-3,4-Cl₂) 2-Me, 6-cPr 0 0 3195 Cl HCO(Ph-3-NO₂-4-Cl) 2-Me 0 0 3196 Cl H CO(Ph-3-NO₂-4-Cl) 2-iPr 0 0 3197 ClH CO(Ph-3-NO₂-4-Cl) 2-cPr 0 0 3198 Cl H CO(Ph-3-NO₂-4-Cl) 2-CH₂CH₂CH₂-30 0 3199 Cl H CO(Ph-3-NO₂-4-Cl) 2,6-Me₂ 0 0 3200 Cl H CO(Ph-3-NO₂-4-Cl)2-Me, 6-cPr 0 0 3201 Cl H CO(Ph-3,5-F₂) 2-Cl 0 0 3202 Cl H CO(Ph-3,5-F₂)2-Br 0 0 3203 Cl H CO(Ph-3,5-F₂) 2-I 0 0 3204 Cl H CO(Ph-3,5-F₂) 2-Me 00 3205 Cl H CO(Ph-3,5-F₂) 2-iPr 0 0 3206 Cl H CO(Ph-3,5-F₂) 2-cPr 0 03207 Cl H CO(Ph-3,5-F₂) 2-cBu 0 0 3208 Cl H CO(Ph-3,5-F₂) 2-CH₂CH₂CH₂-30 0 3209 Cl H CO(Ph-3,5-F₂) 2-cPr, 5-Me 0 0 3210 Cl H CO(Ph-3,5-F₂)2-OMe, 5-Me 0 0 3211 Cl H CO(Ph-3,5-F₂) 2-F, 6-iPr 0 0 3212 Cl HCO(Ph-3,5-F₂) 2-Cl, 6-cPr 0 0 3213 Cl H CO(Ph-3,5-F₂) 2-Br, 6-Me 0 03214 Cl H CO(Ph-3,5-F₂) 2-I, 6-Me 0 0 3215 Cl H CO(Ph-3,5-F₂) 2,6-Me₂ 00 3216 Cl H CO(Ph-3,5-F₂) 2-Me, 6-Et 0 0 3217 Cl H CO(Ph-3,5-F₂) 2-Me,6-cPr 0 0 3218 Cl H CO(Ph-3,5-F₂) 2,6-cPr₂ 0 0 3219 Cl H CO(Ph-3,5-F₂)2-cPr, 3,5-Me₂ 0 0 3220 Cl H CO(Ph-3,5-F₂) 2-cPr, 3,6-Me₂ 0 0 3221 Cl HCO(Ph-3,5-Cl₂) 2-Me 0 0 3222 Cl H CO(Ph-3,5-Cl₂) 2-iPr 0 0 3223 Cl HCO(Ph-3,5-Cl₂) 2-cPr 0 0 3224 Cl H CO(Ph-3,5-Cl₂) 2-CH₂CH₂CH₂-3 0 0 3225Cl H CO(Ph-3,5-Cl₂) 2,6-Me₂ 0 0 3226 Cl H CO(Ph-3,5-Cl₂) 2-Me, 6-cPr 0 03227 Cl H CO(Ph-3,5-Me₂) 2-Cl 0 0 3228 Cl H CO(Ph-3,5-Me₂) 2-Br 0 0 3229Cl H CO(Ph-3,5-Me₂) 2-I 0 0 3230 Cl H CO(Ph-3,5-Me₂) 2-Me 0 0 3231 Cl HCO(Ph-3,5-Me₂) 2-iPr 0 0 3232 Cl H CO(Ph-3,5-Me₂) 2-cPr 0 0 3233 Cl HCO(Ph-3,5-Me₂) 2-cBu 0 0 3234 Cl H CO(Ph-3,5-Me₂) 2-CH₂CH₂CH₂-3 0 0 3235Cl H CO(Ph-3,5-Me₂) 2-cPr, 5-Me 0 0 3236 Cl H CO(Ph-3,5-Me₂) 2-OMe, 5-Me0 0 3237 Cl H CO(Ph-3,5-Me₂) 2-F, 6-iPr 0 0 3238 Cl H CO(Ph-3,5-Me₂)2-Cl, 6-cPr 0 0 3239 Cl H CO(Ph-3,5-Me₂) 2-Br, 6-Me 0 0 3240 Cl HCO(Ph-3,5-Me₂) 2-I, 6-Me 0 0 3241 Cl H CO(Ph-3,5-Me₂) 2,6-Me₂ 0 0 3242Cl H CO(Ph-3,5-Me₂) 2-Me, 6-Et 0 0 3243 Cl H CO(Ph-3,5-Me₂) 2-Me, 6-cPr0 0 3244 Cl H CO(Ph-3,5-Me₂) 2,6-cPr₂ 0 0 3245 Cl H CO(Ph-3,5-Me₂)2-cPr, 3,5-Me₂ 0 0 3246 Cl H CO(Ph-3,5-Me₂) 2-cPr, 3,6-Me₂ 0 0 3247 Cl HCO{Ph-3,5-(OMe)₂} 2-Me 0 0 3248 Cl H CO{Ph-3,5-(OMe)₂} 2-iPr 0 0 3249 ClH CO{Ph-3,5-(OMe)₂} 2-cPr 0 0 3250 Cl H CO{Ph-3,5-(OMe)₂} 2-CH₂CH₂CH₂-30 0 3251 Cl H CO{Ph-3,5-(OMe)₂} 2,6-Me₂ 0 0 3252 Cl H CO{Ph-3,5-(OMe)₂}2-Me, 6-cPr 0 0 3253 Cl H CO(Ph-2,4,6-Cl₃) 2-Me 0 0 3254 Cl HCO(Ph-2,4,6-Cl₃) 2-iPr 0 0 3255 Cl H CO(Ph-2,4,6-Cl₃) 2-cPr 0 0 3256 ClH CO(Ph-2,4,6-Cl₃) 2-CH₂CH₂CH₂-3 0 0 3257 Cl H CO(Ph-2,4,6-Cl₃) 2,6-Me₂0 0 3258 Cl H CO(Ph-2,4,6-Cl₃) 2-Me, 6-cPr 0 0 3259 Cl HCO{Ph-3,4,5-(OMe)₃} 2-Me 0 0 3260 Cl H CO{Ph-3,4,5-(OMe)₃} 2-iPr 0 03261 Cl H CO{Ph-3,4,5-(OMe)₃} 2-cPr 0 0 3262 Cl H CO{Ph-3,4,5-(OMe)₃}2-CH₂CH₂CH₂-3 0 0 3263 Cl H CO{Ph-3,4,5-(OMe)₃} 2,6-Me₂ 0 0 3264 Cl HCO{Ph-3,4,5-(OMe)₃} 2-Me, 6-cPr 0 0 3265 Cl H CO(1-Np) 2-Me 0 0 3266 ClH CO(1-Np) 2-iPr 0 0 3267 Cl H CO(1-Np) 2-cPr 0 0 3268 Cl H CO(1-Np)2-CH₂CH₂CH₂-3 0 0 3269 Cl H CO(1-Np) 2,6-Me₂ 0 0 3270 Cl H CO(1-Np)2-Me, 6-cPr 0 0 3271 Cl H CO(2-Np) 2-Me 0 0 3272 Cl H CO(2-Np) 2-iPr 0 03273 Cl H CO(2-Np) 2-cPr 0 0 3274 Cl H CO(2-Np) 2-CH₂CH₂CH₂-3 0 0 3275Cl H CO(2-Np) 2,6-Me₂ 0 0 3276 Cl H CO(2-Np) 2-Me, 6-cPr 0 0 3277 Cl HCO(2-Pyrr-1-Me) 2-Me 0 0 3278 Cl H CO(2-Pyrr-1-Me) 2-iPr 0 0 3279 Cl HCO(2-Pyrr-1-Me) 2-cPr 0 0 3280 Cl H CO(2-Pyrr-1-Me) 2-CH₂CH₂CH₂-3 0 03281 Cl H CO(2-Pyrr-1-Me) 2,6-Me₂ 0 0 3282 Cl H CO(2-Pyrr-1-Me) 2-Me,6-cPr 0 0 3283 Cl H CO(2-Fur-5-Br) 2-Me 0 0 3284 Cl H CO(2-Fur-5-Br)2-iPr 0 0 3285 Cl H CO(2-Fur-5-Br) 2-cPr 0 0 3286 Cl H CO(2-Fur-5-Br)2-CH₂CH₂CH₂-3 0 0 3287 Cl H CO(2-Fur-5-Br) 2,6-Me₂ 0 0 3288 Cl HCO(2-Fur-5-Br) 2-Me, 6-cPr 0 0 3289 Cl H CO(3-Fur) 2-Me 0 0 3290 Cl HCO(3-Fur) 2-iPr 0 0 3291 Cl H CO(3-Fur) 2-cPr 0 0 3292 Cl H CO(3-Fur)2-CH₂CH₂CH₂-3 0 0 3293 Cl H CO(3-Fur) 2,6-Me₂ 0 0 3294 Cl H CO(3-Fur)2-Me, 6-cPr 0 0 3295 Cl H CO(3-Fur-2-Me-5-tBu) 2-Me 0 0 3296 Cl HCO(3-Fur-2-Me-5-tBu) 2-iPr 0 0 3297 Cl H CO(3-Fur-2-Me-5-tBu) 2-cPr 0 03298 Cl H CO(3-Fur-2-Me-5-tBu) 2-CH₂CH₂CH₂-3 0 0 3299 Cl HCO(3-Fur-2-Me-5-tBu) 2,6-Me₂ 0 0 3300 Cl H CO(3-Fur-2-Me-5-tBu) 2-Me,6-cPr 0 0 3301 Cl H CO(3-Fur-2-CF₃-5-Me) 2-Me 0 0 3302 Cl HCO(3-Fur-2-CF₃-5-Me) 2-iPr 0 0 3303 Cl H CO(3-Fur-2-CF₃-5-Me) 2-cPr 0 03304 Cl H CO(3-Fur-2-CF₃-5-Me) 2-CH₂CH₂CH₂-3 0 0 3305 Cl HCO(3-Fur-2-CF₃-5-Me) 2,6-Me₂ 0 0 3306 Cl H CO(3-Fur-2-CF₃-5-Me) 2-Me,6-cPr 0 0 3307 Cl H CO{3-Fur-2-CF₃-5-(Ph-4-Cl)} 2-Me 0 0 3308 Cl HCO{3-Fur-2-CF₃-5-(Ph-4-Cl)} 2-iPr 0 0 3309 Cl HCO{3-Fur-2-CF₃-5-(Ph-4-Cl)} 2-cPr 0 0 3310 Cl HCO{3-Fur-2-CF₃-5-(Ph-4-Cl)} 2-CH₂CH₂CH₂-3 0 0 3311 Cl HCO{3-Fur-2-CF₃-5-(Ph-4-Cl)} 2,6-Me₂ 0 0 3312 Cl HCO{3-Fur-2-CF₃-5-(Ph-4-Cl)} 2-Me, 6-cPr 0 0 3313 Cl H CO(2-Thi-3-Cl)2-Me 0 0 3314 Cl H CO(2-Thi-3-Cl) 2-iPr 0 0 3315 Cl H CO(2-Thi-3-Cl)2-cPr 0 0 3316 Cl H CO(2-Thi-3-Cl) 2-CH₂CH₂CH₂-3 0 0 3317 Cl HCO(2-Thi-3-Cl) 2,6-Me₂ 0 0 3318 Cl H CO(2-Thi-3-Cl) 2-Me, 6-cPr 0 0 3319Cl H CO(2-Thi-3-Me) 2-Me 0 0 3320 Cl H CO(2-Thi-3-Me) 2-iPr 0 0 3321 ClH CO(2-Thi-3-Me) 2-cPr 0 0 3322 Cl H CO(2-Thi-3-Me) 2-CH₂CH₂CH₂-3 0 03323 Cl H CO(2-Thi-3-Me) 2,6-Me₂ 0 0 3324 Cl H CO(2-Thi-3-Me) 2-Me,6-cPr 0 0 3325 Cl H CO(2-Thi-3-OEt) 2-Me 0 0 3326 Cl H CO(2-Thi-3-OEt)2-iPr 0 0 3327 Cl H CO(2-Thi-3-OEt) 2-cPr 0 0 3328 Cl H CO(2-Thi-3-OEt)2-CH₂CH₂CH₂-3 0 0 3329 Cl H CO(2-Thi-3-OEt) 2,6-Me₂ 0 0 3330 Cl HCO(2-Thi-3-OEt) 2-Me, 6-cPr 0 0 3331 Cl H CO(2-Thi-5-Cl) 2-Me 0 0 3332Cl H CO(2-Thi-5-Cl) 2-iPr 0 0 3333 Cl H CO(2-Thi-5-Cl) 2-cPr 0 0 3334 ClH CO(2-Thi-5-Cl) 2-CH₂CH₂CH₂-3 0 0 3335 Cl H CO(2-Thi-5-Cl) 2,6-Me₂ 0 03336 Cl H CO(2-Thi-5-Cl) 2-Me, 6-cPr 0 0 3337 Cl H CO(2-Thi-5-Br) 2-Me 00 3338 Cl H CO(2-Thi-5-Br) 2-iPr 0 0 3339 Cl H CO(2-Thi-5-Br) 2-cPr 0 03340 Cl H CO(2-Thi-5-Br) 2-CH₂CH₂CH₂-3 0 0 3341 Cl H CO(2-Thi-5-Br)2,6-Me₂ 0 0 3342 Cl H CO(2-Thi-5-Br) 2-Me, 6-cPr 0 0 3343 Cl HCO(2-Thi-5-Me) 2-Me 0 0 3344 Cl H CO(2-Thi-5-Me) 2-iPr 0 0 3345 Cl HCO(2-Thi-5-Me) 2-cPr 0 0 3346 Cl H CO(2-Thi-5-Me) 2-CH₂CH₂CH₂-3 0 0 3347Cl H CO(2-Thi-5-Me) 2,6-Me₂ 0 0 3348 Cl H CO(2-Thi-5-Me) 2-Me, 6-cPr 0 03349 Cl H CO(2-Thi-5-COMe) 2-Me 0 0 3350 Cl H CO(2-Thi-5-COMe) 2-iPr 0 03351 Cl H CO(2-Thi-5-COMe) 2-cPr 0 0 3352 Cl H CO(2-Thi-5-COMe)2-CH₂CH₂CH₂-3 0 0 3353 Cl H CO(2-Thi-5-COMe) 2,6-Me₂ 0 0 3354 Cl HCO(2-Thi-5-COMe) 2-Me, 6-cPr 0 0 3355 Cl H CO(3-Thi-5-NO₂) 2-Me 0 0 3356Cl H CO(3-Thi-5-NO₂) 2-iPr 0 0 3357 Cl H CO(3-Thi-5-NO₂) 2-cPr 0 0 3358Cl H CO(3-Thi-5-NO₂) 2-CH₂CH₂CH₂-3 0 0 3359 Cl H CO(3-Thi-5-NO₂) 2,6-Me₂0 0 3360 Cl H CO(3-Thj-5-NO₂) 2-Me, 6-cPr 0 0 3361 Cl HCO(2-Thi-4,5-Br₂) 2-Me 0 0 3362 Cl H CO(2-Thi-4,5-Br₂) 2-iPr 0 0 3363 ClH CO(2-Thi-4,5-Br₂) 2-cPr 0 0 3364 Cl H CO(2-Thi-4,5-Br₂) 2-CH₂CH₂CH₂-30 0 3365 Cl H CO(2-Thi-4,5-Br₂) 2,6-Me₂ 0 0 3366 Cl H CO(2-Thi-4,5-Br₂)2-Me, 6-cPr 0 0 3367 Cl H CO(3-Thi) 2-Me 0 0 3368 Cl H CO(3-Thi) 2-iPr 00 3369 Cl H CO(3-Thi) 2-cPr 0 0 3370 Cl H CO(3-Thi) 2-CH₂CH₂CH₂-3 0 03371 Cl H CO(3-Thi) 2,6-Me₂ 0 0 3372 Cl H CO(3-Thi) 2-Me, 6-cPr 0 0 3373Cl H CO(3-Thi-4-OMe) 2-Me 0 0 3374 Cl H CO(3-Thi-4-OMe) 2-iPr 0 0 3375Cl H CO(3-Thi-4-OMe) 2-cPr 0 0 3376 Cl H CO(3-Thi-4-OMe) 2-CH₂CH₂CH₂-3 00 3377 Cl H CO(3-Thi-4-OMe) 2,6-Me₂ 0 0 3378 Cl H CO(3-Thi-4-OMe) 2-Me,6-cPr 0 0 3379 Cl H CO(5-Pyza-1-CH₂Ph-3-tBu) 2-Me 0 0 3380 Cl HCO(5-Pyza-1-CH₂Ph-3-tBu) 2-iPr 0 0 3381 Cl H CO(5-Pyza-1-CH₂Ph-3-tBu)2-cPr 0 0 3382 Cl H CO(5-Pyza-1-CH₂Ph-3-tBu) 2-CH₂CH₂CH₂-3 0 0 3383 Cl HCO(5-Pyza-1-CH₂Ph-3-tBu) 2,6-Me₂ 0 0 3384 Cl H CO(5-Pyza-1-CH₂Ph-3-tBu)2-Me, 6-cPr 0 0 3385 Cl H CO(4-Pyza-1,3-Me₂-5-Cl) 2-Me 0 0 3386 Cl HCO(4-Pyza-1,3-Me₂-5-Cl) 2-iPr 0 0 3387 Cl H CO(4-Pyza-1,3-Me₂-5-Cl)2-cPr 0 0 3388 Cl H CO(4-Pyza-1,3-Me₂-5-Cl) 2-CH₂CH₂CH₂-3 0 0 3389 Cl HCO(4-Pyza-1,3-Me₂-5-Cl) 2,6-Me₂ 0 0 3390 Cl H CO(4-Pyza-1,3-Me₂-5-Cl)2-Me, 6-cPr 0 0 3391 Cl H CO{4-Ioxa-5-Me-3-(Ph-2-Cl)} 2-Me 0 0 3392 Cl HCO{4-Ioxa-5-Me-3-(Ph-2-Cl)} 2-iPr 0 0 3393 Cl HCO{4-Ioxa-5-Me-3-(Ph-2-Cl)} 2-cPr 0 0 3394 Cl HCO{4-Ioxa-5-Me-3-(Ph-2-Cl)} 2-CH₂CH₂CH₂-3 0 0 3395 Cl HCO{4-Ioxa-5-Me-3-(Ph-2-Cl)} 2,6-Me₂ 0 0 3396 Cl HCO{4-Ioxa-5-Me-3-(Ph-2-Cl)} 2-Me, 6-cPr 0 0 3397 Cl H CO(5-Tdia-4-Me)2-Me 0 0 3398 Cl H CO(5-Tdia-4-Me) 2-iPr 0 0 3399 Cl H CO(5-Tdia-4-Me)2-cPr 0 0 3400 Cl H CO(5-Tdia-4-Me) 2-CH₂CH₂CH₂-3 0 0 3401 Cl HCO(5-Tdia-4-Me) 2,6-Me₂ 0 0 3402 Cl H CO(5-Tdia-4-Me) 2-Me, 6-cPr 0 03403 Cl H CO(2-Pyr-6-Me) 2-Me 0 0 3404 Cl H CO(2-Pyr-6-Me) 2-iPr 0 03405 Cl H CO(2-Pyr-6-Me) 2-cPr 0 0 3406 Cl H CO(2-Pyr-6-Me)2-CH₂CH₂CH₂-3 0 0 3407 Cl H CO(2-Pyr-6-Me) 2,6-Me₂ 0 0 3408 Cl HCO(2-Pyr-6-Me) 2-Me, 6-cPr 0 0 3409 Cl H CO(2-Pyr-5-Bu) 2-Me 0 0 3410 ClH CO(2-Pyr-5-Bu) 2-iPr 0 0 3411 Cl H CO(2-Pyr-5-Bu) 2-cPr 0 0 3412 Cl HCO(2-Pyr-5-Bu) 2-CH₂CH₂CH₂-3 0 0 3413 Cl H CO(2-Pyr-5-Bu) 2,6-Me₂ 0 03414 Cl H CO(2-Pyr-5-Bu) 2-Me, 6-cPr 0 0 3415 Cl H CO(3-Pyr) 2-Me 0 03416 Cl H CO(3-Pyr) 2-iPr 0 0 3417 Cl H CO(3-Pyr) 2-cPr 0 0 3418 Cl HCO(3-Pyr) 2-CH₂CH₂CH₂-3 0 0 3419 Cl H CO(3-Pyr) 2,6-Me₂ 0 0 3420 Cl HCO(3-Pyr) 2-Me, 6-cPr 0 0 3421 Cl H CO(3-Pyr-2-Cl) 2-Me 0 0 3422 Cl HCO(3-Pyr-2-Cl) 2-iPr 0 0 3423 Cl H CO(3-Pyr-2-Cl) 2-cPr 0 0 3424 Cl HCO(3-Pyr-2-Cl) 2-CH₂CH₂CH₂-3 0 0 3425 Cl H CO(3-Pyr-2-Cl) 2,6-Me₂ 0 03426 Cl H CO(3-Pyr-2-Cl) 2-Me, 6-cPr 0 0 3427 Cl H CO(3-Pyr-2-Me) 2-Me 00 3428 Cl H CO(3-Pyr-2-Me) 2-iPr 0 0 3429 Cl H CO(3-Pyr-2-Me) 2-cPr 0 03430 Cl H CO(3-Pyr-2-Me) 2-CH₂CH₂CH₂-3 0 0 3431 Cl H CO(3-Pyr-2-Me)2,6-Me₂ 0 0 3432 Cl H CO(3-Pyr-2-Me) 2-Me, 6-cPr 0 0 3433 Cl HCO(3-Pyr-2-OPh) 2-Me 0 0 3434 Cl H CO(3-Pyr-2-OPh) 2-iPr 0 0 3435 Cl HCO(3-Pyr-2-OPh) 2-cPr 0 0 3436 Cl H CO(3-Pyr-2-OPh) 2-CH₂CH₂CH₂-3 0 03437 Cl H CO(3-Pyr-2-OPh) 2,6-Me₂ 0 0 3438 Cl H CO(3-Pyr-2-OPh) 2-Me,6-cPr 0 0 3439 Cl H CO(3-Pyr-2-SMe) 2-Me 0 0 3440 Cl H CO(3-Pyr-2-SMe)2-iPr 0 0 3441 Cl H CO(3-Pyr-2-SMe) 2-cPr 0 0 3442 Cl H CO(3-Pyr-2-SMe)2-CH₂CH₂CH₂-3 0 0 3443 Cl H CO(3-Pyr-2-SMe) 2,6-Me₂ 0 0 3444 Cl HCO(3-Pyr-2-SMe) 2-Me, 6-cPr 0 0 3445 Cl H CO(3-Pyr-2-SCH₂CH═CH₂) 2-Me 00 3446 Cl H CO(3-Pyr-2-SCH₂CH═CH₂) 2-iPr 0 0 3447 Cl HCO(3-Pyr-2-SCH₂CH═CH₂) 2-cPr 0 0 3448 Cl H CO(3-Pyr-2-SCH₂CH═CH₂)2-CH₂CH₂CH₂-3 0 0 3449 Cl H CO(3-Pyr-2-SCH₂CH═CH₂) 2,6-Me₂ 0 0 3450 Cl HCO(3-Pyr-2-SCH₂CH═CH₂) 2-Me, 6-cPr 0 0 3451 Cl H CO(3-Pyr-2-SPh) 2-Me 00 3452 Cl H CO(3-Pyr-2-SPh) 2-iPr 0 0 3453 Cl H CO(3-Pyr-2-SPh) 2-cPr 00 3454 Cl H CO(3-Pyr-2-SPh) 2-CH₂CH₂CH₂-3 0 0 3455 Cl H CO(3-Pyr-2-SPh)2,6-Me₂ 0 0 3456 Cl H CO(3-Pyr-2-SPh) 2-Me, 6-cPr 0 0 3457 Cl HCO(3-Pyr-4-CF₃) 2-Me 0 0 3458 Cl H CO(3-Pyr-4-CF₃) 2-iPr 0 0 3459 Cl HCO(3-Pyr-4-CF₃) 2-cPr 0 0 3460 Cl H CO(3-Pyr-4-CF₃) 2-CH₂CH₂CH₂-3 0 03461 Cl H CO(3-Pyr-4-CF₃) 2,6-Me₂ 0 0 3462 Cl H CO(3-Pyr-4-CF₃) 2-Me,6-cPr 0 0 3463 Cl H CO(3-Pyr-6-Cl) 2-Me 0 0 3464 Cl H CO(3-Pyr-6-Cl)2-iPr 0 0 3465 Cl H CO(3-Pyr-6-Cl) 2-cPr 0 0 3466 Cl H CO(3-Pyr-6-Cl)2-CH₂CH₂CH₂-3 0 0 3467 Cl H CO(3-Pyr-6-Cl) 2,6-Me₂ 0 0 3468 Cl HCO(3-Pyr-6-Cl) 2-Me, 6-cPr 0 0 3469 Cl H CO(3-Pyr-2,6-Cl₂) 2-Me 0 0 3470Cl H CO(3-Pyr-2,6-Cl₂) 2-iPr 0 0 3471 Cl H CO(3-Pyr-2,6-Cl₂) 2-cPr 0 03472 Cl H CO(3-Pyr-2,6-Cl₂) 2-CH₂CH₂CH₂-3 0 0 3473 Cl HCO(3-Pyr-2,6-Cl₂) 2,6-Me₂ 0 0 3474 Cl H CO(3-Pyr-2,6-Cl₂) 2-Me, 6-cPr 00 3475 Cl H CO(3-Pyr-2-Cl-6-Me) 2-Me 0 0 3476 Cl H CO(3-Pyr-2-Cl-6-Me)2-iPr 0 0 3477 Cl H CO(3-Pyr-2-Cl-6-Me) 2-cPr 0 0 3478 Cl HCO(3-Pyr-2-Cl-6-Me) 2-CH₂CH₂CH₂-3 0 0 3479 Cl H CO(3-Pyr-2-Cl-6-Me)2,6-Me₂ 0 0 3480 Cl H CO(3-Pyr-2-Cl-6-Me) 2-Me, 6-cPr 0 0 3481 Cl HCO(3-Pyr-5,6-Cl₂) 2-Me 0 0 3482 Cl H CO(3-Pyr-5,6-Cl₂) 2-iPr 0 0 3483 ClH CO(3-Pyr-5,6-Cl₂) 2-cPr 0 0 3484 Cl H CO(3-Pyr-5,6-Cl₂) 2-CH₂CH₂CH₂-30 0 3485 Cl H CO(3-Pyr-5,6-Cl₂) 2,6-Me₂ 0 0 3486 Cl H CO(3-Pyr-5,6-Cl₂)2-Me, 6-cPr 0 0 3487 Cl H CO(4-Pyr-2-Cl) 2-Me 0 0 3488 Cl HCO(4-Pyr-2-Cl) 2-iPr 0 0 3489 Cl H CO(4-Pyr-2-Cl) 2-cPr 0 0 3490 Cl HCO(4-Pyr-2-Cl) 2-CH₂CH₂CH₂-3 0 0 3491 Cl H CO(4-Pyr-2-Cl) 2,6-Me₂ 0 03492 Cl H CO(4-Pyr-2-Cl) 2-Me, 6-cPr 0 0 3493 Cl H CO(2-Bfur) 2-Me 0 03494 Cl H CO(2-Bfur) 2-iPr 0 0 3495 Cl H CO(2-Bfur) 2-cPr 0 0 3496 Cl HCO(2-Bfur) 2-CH₂CH₂CH₂-3 0 0 3497 Cl H CO(2-Bfur) 2,6-Me₂ 0 0 3498 Cl HCO(2-Bfur) 2-Me, 6-cPr 0 0 3499 Cl H CO(2-Bthi) 2-Me 0 0 3500 Cl HCO(2-Bthi) 2-iPr 0 0 3501 Cl H CO(2-Bthi) 2-cPr 0 0 3502 Cl H CO(2-Bthi)2-CH₂CH₂CH₂-3 0 0 3503 Cl H CO(2-Bthi) 2,6-Me₂ 0 0 3504 Cl H CO(2-Bthi)2-Me, 6-cPr 0 0 3505 Cl H CO(6-Bthia) 2-Me 0 0 3506 Cl H CO(6-Bthia)2-iPr 0 0 3507 Cl H CO(6-Bthia) 2-cPr 0 0 3508 Cl H CO(6-Bthia)2-CH₂CH₂CH₂-3 0 0 3509 Cl H CO(6-Bthia) 2,6-Me₂ 0 0 3510 Cl HCO(6-Bthia) 2-Me, 6-cPr 0 0 3511 Cl H CO(5-Boxaz) 2-Me 0 0 3512 Cl HCO(5-Boxaz) 2-iPr 0 0 3513 Cl H CO(5-Boxaz) 2-cPr 0 0 3514 Cl HCO(5-Boxaz) 2-CH₂CH₂CH₂-3 0 0 3515 Cl H CO(5-Boxaz) 2,6-Me₂ 0 0 3516 ClH CO(5-Boxaz) 2-Me, 6-cPr 0 0 3517 Cl H CO(1-Iqu) 2-Me 0 0 3518 Cl HCO(1-Iqu) 2-iPr 0 0 3519 Cl H CO(1-Iqu) 2-cPr 0 0 3520 Cl H CO(1-Iqu)2-CH₂CH₂CH₂-3 0 0 3521 Cl H CO(1-Iqu) 2,6-Me₂ 0 0 3522 Cl H CO(1-Iqu)2-Me, 6-cPr 0 0 3523 Cl H CONMe(tBu) 2-Me 0 0 3524 Cl H CONMe(tBu) 2-iPr0 0 3525 Cl H CONMe(tBu) 2-cPr 0 0 3526 Cl H CONMe(tBu) 2-CH₂CH₂CH₂-3 00 3527 Cl H CONMe(tBu) 2,6-Me₂ 0 0 3528 Cl H CONMe(tBu) 2-Me, 6-cPr 0 03529 Cl H CONBu₂ 2-Me 0 0 3530 Cl H CONBu₂ 2-iPr 0 0 3531 Cl H CONBu₂2-cPr 0 0 3532 Cl H CONBu₂ 2-CH₂CH₂CH₂-3 0 0 3533 Cl H CONBu₂ 2,6-Me₂ 00 3534 Cl H CONBu₂ 2-Me, 6-cPr 0 0 3535 Cl H CONMe(CH₂Ph) 2-Me 0 0 3536Cl H CONMe(CH₂Ph) 2-iPr 0 0 3537 Cl H CONMe(CH₂Ph) 2-cPr 0 0 3538 Cl HCONMe(CH₂Ph) 2-CH₂CH₂CH₂-3 0 0 3539 Cl H CONMe(CH₂Ph) 2,6-Me₂ 0 0 3540Cl H CONMe(CH₂Ph) 2-Me, 6-cPr 0 0 3541 Cl H CONMe(CH₂CN) 2-Me 0 0 3542Cl H CONMe(CH₂CN) 2-iPr 0 0 3543 Cl H CONMe(CH₂CN) 2-cPr 0 0 3544 Cl HCONMe(CH₂CN) 2CH₂CH₂CH₂-3 0 0 3545 Cl H CONMe(CH₂CN) 2,6-Me₂ 0 0 3546 ClH CONMe(CH₂CN) 2-Me, 6-cPr 0 0 3547 Cl H CONMe(CH₂CO₂Et) 2-Me 0 0 3548Cl H CONMe(CH₂CO₂Et) 2-iPr 0 0 3549 Cl H CONMe(CH₂CO₂Et) 2-cPr 0 0 3550Cl H CONMe(CH₂CO₂Et) 2-CH₂CH₂CH₂-3 0 0 3551 Cl H CONMe(CH₂CO₂Et) 2,6-Me₂0 0 3552 Cl H CONMe(CH₂CO₂Et) 2-Me, 6-cPr 0 0 3553 Cl H CONMe(2-Pyr)2-Me 0 0 3554 Cl H CONMe(2-Pyr) 2-iPr 0 0 3555 Cl H CONMe(2-Pyr) 2-cPr 00 3556 Cl H CONMe(2-Pyr) 2-CH₂CH₂CH₂-3 0 0 3557 Cl H CONMe(2-Pyr)2,6-Me₂ 0 0 3558 Cl H CONMe(2-Pyr) 2-Me, 6-cPr 0 0 3559 Cl H CONMe(OMe)2-Me 0 0 3560 Cl H CONMe(OMe) 2-iPr 0 0 3561 Cl H CONMe(OMe) 2-cPr 0 03562 Cl H CONMe(OMe) 2-CH₂CH₂CH₂-3 0 0 3563 Cl H CONMe(OMe) 2,6-Me₂ 0 03564 Cl H CONMe(OMe) 2-Me, 6-cPr 0 0 3565 Cl H CON(CH₂CH₂Cl)₂ 2-Me 0 03566 Cl H CON(CH₂CH₂Cl)₂ 2-iPr 0 0 3567 Cl H CON(CH₂CH₂Cl)₂ 2-cPr 0 03568 Cl H CON(CH₂CH₂Cl)₂ 2-CH₂CH₂CH₂-3 0 0 3569 Cl H CON(CH₂CH₂Cl)₂2,6-Me₂ 0 0 3570 Cl H CON(CH₂CH₂Cl)₂ 2-Me, 6-cPr 0 0 3571 Cl HCON(CH₂CH═CH₂)₂ 2-Me 0 0 3572 Cl H CON(CH₂CH═CH₂)₂ 2-iPr 0 0 3573 Cl HCON(CH₂CH═CH₂)₂ 2-cPr 0 0 3574 Cl H CON(CH₂CH═CH₂)₂ 2-CH₂CH₂CH₂-3 0 03575 Cl H CON(CH₂CH═CH₂)₂ 2,6-Me₂ 0 0 3576 Cl H CON(CH₂CH═CH₂)₂ 2-Me,6-cPr 0 0 3577 Cl H CON(CH₂CN)₂ 2-Me 0 0 3578 Cl H CON(CH₂CN)₂ 2-iPr 0 03579 Cl H CON(CH₂CN)₂ 2-cPr 0 0 3580 Cl H CON(CH₂CN)₂ 2-CH₂CH₂CH₂-3 0 03581 Cl H CON(CH₂CN)₂ 2,6-Me₂ 0 0 3582 Cl H CON(CH₂CN)₂ 2-Me, 6-cPr 0 03583 Cl H CON(CH₂CH₂CN)₂ 2-Me 0 0 3584 Cl H CON(CH₂CH₂CN)₂ 2-iPr 0 03585 Cl H CON(CH₂CH₂CN)₂ 2-cPr 0 0 3586 Cl H CON(CH₂CH₂CN)₂2-CH₂CH₂CH₂-3 0 0 3587 Cl H CON(CH₂CH₂CN)₂ 2,6-Me₂ 0 0 3588 Cl HCON(CH₂CH₂CN)₂ 2-Me, 6-cPr 0 0 3589 Cl H CON(CH₂CO₂Et)₂ 2-Me 0 0 3590 ClH CON(CH₂CO₂Et)₂ 2-iPr 0 0 3591 Cl H CON(CH₂CO₂Et)₂ 2-cPr 0 0 3592 Cl HCON(CH₂cO₂Et)₂ 2-CH₂CH₂CH₂-3 0 0 3593 Cl H CON(CH₂CO₂Et)₂ 2,6-Me₂ 0 03594 Cl H CON(CH₂CO₂Et)₂ 2-Me, 6-cPr 0 0 3595 Cl H CON(CH₂CH₂OMe)₂ 2-Me0 0 3596 Cl H CON(CH₂CH₂OMe)₂ 2-iPr 0 0 3597 Cl H CON(CH₂CH₂OMe)₂ 2-cPr0 0 3598 Cl H CON(CH₂CH₂OMe)₂ 2-CH₂CH₂CH₂-3 0 0 3599 Cl HCON(CH₂CH₂OMe)₂ 2,6-Me₂ 0 0 3600 Cl H CON(CH₂CH₂OMe)₂ 2-Me, 6-cPr 0 03601 Cl H CON(CH₂CH₂OEt)₂ 2-Me 0 0 3602 Cl H CON(CH₂CH₂OEt)₂ 2-iPr 0 03603 Cl H CON(CH₂CH₂OEt)₂ 2-cPr 0 0 3604 Cl H CON(CH₂CH₂OEt)₂2-CH₂CH₂CH₂-3 0 0 3605 Cl H CON(CH₂CH₂OEt)₂ 2,6-Me₂ 0 0 3606 Cl HCON(CH₂CH₂OEt)₂ 2-Me, 6-cPr 0 0 3607 Cl H CO(1-Azet) 2-Me 0 0 3608 Cl HCO(1-Azet) 2-iPr 0 0 3609 Cl H CO(1-Azet) 2-cPr 0 0 3610 Cl H CO(1-Azet)2-CH₂CH₂CH₂-3 0 0 3611 Cl H CO(1-Azet) 2,6-Me₂ 0 0 3612 Cl H CO(1-Azet)2-Me, 6-cPr 0 0 3613 Cl H CO(1-Pyrd-2-CO₂Me) 2-Me 0 0 3614 Cl HCO(1-Pyrd-2-CO₂Me) 2-iPr 0 0 3615 Cl H CO(1-Pyrd-2-CO₂Me) 2-cPr 0 0 3616Cl H CO(1-Pyrd-2-CO₂Me) 2-CH₂CH₂CH₂-3 0 0 3617 Cl H CO(1-Pyrd-2-CO₂Me)2,6-Me₂ 0 0 3618 Cl H CO(1-Pyrd-2-CO₂Me) 2-Me, 6-cPr 0 0 3619 Cl HCO(1-Pyrd-3-OH) 2-Me 0 0 3620 Cl H CO(1-Pyrd-3-OH) 2-iPr 0 0 3621 Cl HCO(1-Pyrd-3-OH) 2-cPr 0 0 3622 Cl H CO(1-Pyrd-3-OH) 2-CH₂CH₂CH₂-3 0 03623 Cl H CO(1-Pyrd-3-OH) 2,6-Me₂ 0 0 3624 Cl H CO(1-Pyrd-3-OH) 2-Me,6-cPr 0 0 3625 Cl H CO(1-Pyrr-2,5-Me₂) 2-Me 0 0 3626 Cl HCO(1-Pyrr-2,5-Me₂) 2-iPr 0 0 3627 Cl H CO(1-Pyrr-2,5-Me₂) 2-cPr 0 0 3628Cl H CO(1-Pyrr-2,5-Me₂) 2-CH₂CH₂CH₂-3 0 0 3629 Cl H CO(1-Pyrr-2,5-Me₂)2,6-Me₂ 0 0 3630 Cl H CO(1-Pyrr-2,5-Me₂) 2-Me, 6-cPr 0 0 3631 Cl HCO(1-Ppri) 2-Me 0 0 3632 Cl H CO(1-Ppri) 2-iPr 0 0 3633 Cl H CO(1-Ppri)2-cPr 0 0 3634 Cl H CO(1-Ppri) 2-CH₂CH₂CH₂-3 0 0 3635 Cl H CO(1-Ppri)2,6-Me₂ 0 0 3636 Cl H CO(1-Ppri) 2-Me, 6-cPr 0 0 3637 Cl HCO(1-Ppri-2-CO₂Me) 2-Me 0 0 3638 Cl H CO(1-Ppri-2-CO₂Me) 2-iPr 0 0 3639Cl H CO(1-Ppri-2-CO₂Me) 2-cPr 0 0 3640 Cl H CO(1-Ppri-2-CO₂Me)2-CH₂CH₂CH₂-3 0 0 3641 Cl H CO(1-Ppri-2-CO₂Me) 2,6-Me₂ 0 0 3642 Cl HCO(1-Ppri-2-CO₂Me) 2-Me, 6-cPr 0 0 3643 Cl H CO(1-Ppri-4-Br) 2-Me 0 03644 Cl H CO(1-Ppri-4-Br) 2-iPr 0 0 3645 Cl H CO(1-Ppri-4-Br) 2-cPr 0 03646 Cl H CO(1-Ppri-4-Br) 2-CH₂CH₂CH₂-3 0 0 3647 Cl H CO(1-Ppri-4-Br)2,6-Me₂ 0 0 3648 Cl H CO(1-Ppri-4-Br) 2-Me, 6-cPr 0 0 3649 Cl HCO(1-Ppri-4-Me) 2-Me 0 0 3650 Cl H CO(1-Ppri-4-Me) 2-iPr 0 0 3651 Cl HCO(1-Ppri-4-Me) 2-cPr 0 0 3652 Cl H CO(1-Ppri-4-Me) 2-CH₂CH₂CH₂-3 0 03653 Cl H CO(1-Ppri-4-Me) 2,6-Me₂ 0 0 3654 Cl H CO(1-Ppri-4-Me) 2-Me,6-cPr 0 0 3655 Cl H CO(1-Ppri-4-CO₂Me) 2-Me 0 0 3656 Cl HCO(1-Ppri-4-CO₂Me) 2-iPr 0 0 3657 Cl H CO(1-Ppri-4-CO₂Me) 2-cPr 0 0 3658Cl H CO(1-Ppri-4-CO₂Me) 2-CH₂CH₂CH₂-3 0 0 3659 Cl H CO(1-Ppri-4-CO₂Me)2,6-Me₂ 0 0 3660 Cl H CO(1-Ppri-4-CO₂Et) 2-Me, 6-cPr 0 0 3661 Cl HCO(1-Ppri-4-OCH₂CH₂O-4) 2-Me 0 0 3662 Cl H CO(1-Ppri-4-OCH₂CH₂O-4) 2-iPr0 0 3663 Cl H CO(1-Ppri-4-OCH₂CH₂O-4) 2-cPr 0 0 3664 Cl HCO(1-Ppri-4-OCH₂CH₂O-4) 2-CH₂CH₂CH₂-3 0 0 3665 Cl HCO(1-Ppri-4-OCH₂CH₂O-4) 2,6-Me₂ 0 0 3666 Cl H CO(1-Ppri-4-OCH₂CH₂O-4)2-Me, 6-cPr 0 0 3667 Cl H CO(1-Ppri-2,2,6,6-Me₄) 2-Me 0 0 3668 Cl HCO(1-Ppri-2,2,6,6-Me₄) 2-iPr 0 0 3669 Cl H CO(1-Ppri-2,2,6,6-Me₄) 2-cPr0 0 3670 Cl H CO(1-Ppri-2,2,6,6-Me₄) 2-CH₂CH₂CH₂-3 0 0 3671 Cl HCO(1-Ppri-2,2,6,6-Me₄) 2,6-Me₂ 0 0 3672 Cl H CO(1-Ppri-2,2,6,6-Me₄)2-Me, 6-cPr 0 0 3673 Cl H CO(1-Ppra-4-Me) 2-Me 0 0 3674 Cl HCO(1-Ppra-4-Me) 2-iPr 0 0 3675 Cl H CO(1-Ppra-4-Me) 2-cPr 0 0 3676 Cl HCO(1-Ppra-4-Me) 2-CH₂CH₂CH₂-3 0 0 3677 Cl H CO(1-Ppra-4-Me) 2,6-Me₂ 0 03678 Cl H CO(1-Ppra-4-Me) 2-Me, 6-cPr 0 0 3679 Cl H CO(1-Ppra-4-Ph) 2-Me0 0 3680 Cl H CO(1-Ppra-4-Ph) 2-iPr 0 0 3681 Cl H CO(1-Ppra-4-Ph) 2-cPr0 0 3682 Cl H CO(1-Ppra-4-Ph) 2-CH₂CH₂CH₂-3 0 0 3683 Cl HCO(1-Ppra-4-Ph) 2,6-Me₂ 0 0 3684 Cl H CO(1-Ppra-4-Ph) 2-Me, 6-cPr 0 03685 Cl H CO-4-Morp 2-Me 0 0 3686 Cl H CO-4-Morp 2-iPr 0 0 3687 Cl HCO-4-Morp 2-cPr 0 0 3688 Cl H CO-4-Morp 2-CH₂CH₂CH₂-3 0 0 3689 Cl HCO-4-Morp 2,6-Me₂ 0 0 3690 Cl H CO-4-Morp 2-Me, 6-cPr 0 0 3691 Cl HCO(4-Morp-2,6-Me₂) 2-Me 0 0 3692 Cl H CO(4-Morp-2,6-Me₂) 2-iPr 0 0 3693Cl H CO(4-Morp-2,6-Me₂) 2-cPr 0 0 3694 Cl H CO(4-Morp-2,6-Me₂)2-CH₂CH₂CH₂-3 0 0 3695 Cl H CO(4-Morp-2,6-Me₂) 2,6-Me₂ 0 0 3696 Cl HCO(4-Morp-2,6-Me₂) 2-Me, 6-cPr 0 0 3697 Cl H CO-4-Tmor 2-Me 0 0 3698 ClH CO-4-Tmor 2-iPr 0 0 3699 Cl H CO-4-Tmor 2-cPr 0 0 3700 Cl H CO-4-Tmor2-CH₂CH₂CH₂-3 0 0 3701 Cl H CO-4-Tmor 2,6-Me₂ 0 0 3702 Cl H CO-4-Tmor2-Me, 6-cPr 0 0 3703 Cl H COQ¹⁸ 2-Me 0 0 3704 Cl H COQ¹⁸ 2-iPr 0 0 3705Cl H COQ¹⁸ 2-cPr 0 0 3706 Cl H COQ¹⁸ 2-CH₂CH₂CH₂-3 0 0 3707 Cl H COQ¹⁸2,6-Me₂ 0 0 3708 Cl H COQ¹⁸ 2-Me, 6-cPr 0 0 3709 Cl H CO(9-Carb) 2-Me 00 3710 Cl H CO(9-Carb) 2-iPr 0 0 3711 Cl H CO(9-Carb) 2-cPr 0 0 3712 ClH CO(9-Carb) 2-CH₂CH₂CH₂-3 0 0 3713 Cl H CO(9-Carb) 2,6-Me₂ 0 0 3714 ClH CO(9-Carb) 2-Me, 6-cPr 0 0 3715 Cl H CO(10-Pthia) 2-Me 0 0 3716 Cl HCO(10-Pthia) 2-iPr 0 0 3717 Cl H CO(10-Pthia) 2-cPr 0 0 3718 Cl HCO(10-Pthia) 2-CH₂CH₂CH₂-3 0 0 3719 Cl H CO(10-Pthia) 2,6-Me₂ 0 0 3720Cl H CO(10-Pthia) 2-Me, 6-cPr 0 0 3721 Cl H SO₂ (Ph-2-CO₂Q⁵) 2-Me, 6-cPr0 0 3722 Cl H SO₂ (Ph-3-CO₂Q⁵) 2-Me, 6-cPr 0 0 3723 Cl H SO₂(Ph-4-CO₂Q⁵) 2-Me, 6-cPr 0 0 3724 Cl H SO₂ (Ph-4-OMe) 2-Cl 0 0 3725 Cl HSO₂ (Ph-4-OMe) 2-Br 0 0 3726 Cl H SO₂ (Ph-4-OMe) 2-I 0 0 3727 Cl H SO₂(Ph-4-OMe) 2-cBu 0 0 3728 Cl H SO₂ (Ph-4-OMe) 2-cPr, 5-Me 0 0 3729 Cl HSO₂ (Ph-4-OMe) 2-OMe, 5-Me 0 0 3730 Cl H SO₂ (Ph-4-OMe) 2-F, 6-iPr 0 03731 Cl H SO₂ (Ph-4-OMe) 2-Cl, 6-cPr 0 0 3732 Cl H SO₂ (Ph-4-OMe) 2-Br,6-Me 0 0 3733 Cl H SO₂ (Ph-4-OMe) 2-I, 6-Me 0 0 3734 Cl H SO₂ (Ph-4-OMe)2-Me, 6-Et 0 0 3735 Cl H SO₂ (Ph-4-OMe) 2,6-cPr₂ 0 0 3736 Cl H SO₂(Ph-4-OMe) 2-cPr, 3,5-Me₂ 0 0 3737 Cl H SO₂ (Ph-4-OMe) 2-cPr, 3,6-Me₂ 00 3738 Cl H SO₂ (Ph-2-SO₂OQ⁶) 2-Me 0 0 3739 Cl H SO₂ (Ph-2-SO₂OQ⁷) 2-iPr0 0 3740 Cl H SO₂ (Ph-2-SO₂OQ⁸) 2-cPr 0 0 3741 Cl H SO₂ (Ph-2-SO₂OQ⁹)2-CH₂CH₂CH₂-3 0 0 3742 Cl H SO₂ (Ph-2-SO₂OQ¹⁰) 2,6-Me₂ 0 0 3743 Cl H SO₂(Ph-2-SO₂OQ¹¹) 2-Me, 6-cPr 0 0 3744 Cl H SO₂ (Ph-2-SO₂OQ¹²) 2-Me, 6-cPr0 0 3745 Cl H SO₂ (Ph-2-SO₂OQ¹³) 2-Me, 6-cPr 0 0 3746 Cl H SO₂(Ph-2-SO₂OQ¹⁴) 2-Me, 6-cPr 0 0 3747 Cl H SO₂ (Ph-2-SO₂OQ¹⁵) 2-Me, 6-cPr0 0 3748 Cl H SO₂ (Ph-2-SO₂OQ¹⁶) 2-Me, 6-cPr 0 0 3749 Cl H SO₂(Ph-2-SO₂OQ¹⁷) 2-Me, 6-cPr 0 0 3750 Cl H SO₂ (Ph-3-SO₂OQ⁶) 2-Me 0 0 3751Cl H SO₂ (Ph-3-SO₂OQ⁷) 2-iPr 0 0 3752 Cl H SO₂ (Ph-3-SO₂OQ⁸) 2-cPr 0 03753 Cl H SO₂ (Ph-3-SO₂OQ⁹) 2-CH₂CH₂CH₂-3 0 0 3754 Cl H SO₂(Ph-3-SO₂OQ¹⁰) 2,6-Me₂ 0 0 3755 Cl H SO₂ (Ph-3-SO₂OQ¹¹) 2-Me, 6-cPr 0 03756 Cl H SO₂ (Ph-3-SO₂OQ¹²) 2-Me, 6-cPr 0 0 3757 Cl H SO₂(Ph-3-SO₂OQ¹³) 2-Me, 6-cPr 0 0 3758 Cl H SO₂ (Ph-3-SO₂OQ¹⁴) 2-Me, 6-cPr0 0 3759 Cl H SO₂ (Ph-3-SO₂OQ¹⁵) 2-Me, 6-cPr 0 0 3760 Cl H SO₂(Ph-3-SO₂OQ¹⁶) 2-Me, 6-cPr 0 0 3761 Cl H SO₂ (Ph-3-SO₂OQ¹⁷) 2-Me, 6-cPr0 0 3762 Cl H SO₂ (Ph-4-SO₂OQ⁵) 2-Cl, 6-cPr 0 0 3763 Cl H SO₂(Ph-4-SO₂OQ⁶) 2-Me 0 0 3764 Cl H SO₂ (Ph-4-SO₂OQ⁷) 2-iPr 0 0 3765 Cl HSO₂ (Ph-4-SO₂OQ⁸) 2-cPr 0 0 3766 Cl H SO₂ (Ph-4-SO₂OQ⁹) 2-CH₂CH₂CH₂-3 00 3767 Cl H SO₂ (Ph-4-SO₂OQ¹⁰) 2,6-Me₂ 0 0 3768 Cl H SO₂ (Ph-4-SO₂OQ¹¹)2-Me, 6-cPr 0 0 3769 Cl H SO₂ (Ph-4-SO₂OQ¹²) 2-Me, 6-cPr 0 0 3770 Cl HSO₂ (Ph-4-SO₂OQ¹³) 2-Me, 6-cPr 0 0 3771 Cl H SO₂ (Ph-4-SO₂OQ¹⁴) 2-Me,6-cPr 0 0 3772 Cl H SO₂ (Ph-4-SO₂OQ¹⁵) 2-Me, 6-cPr 0 0 3773 Cl H SO₂(Ph-4-SO₂OQ¹⁶) 2-Me, 6-cPr 0 0 3774 Cl H SO₂ (Ph-4-SO₂OQ¹⁷) 2-Me, 6-cPr0 0 3775 Cl H SO₂ (Ph-2,5-Cl₂) 2-Me 0 0 3776 Cl H SO₂ (Ph-2,5-Cl₂) 2-iPr0 0 3777 Cl H SO₂ (Ph-2,5-Cl₂) 2-cPr 0 0 3778 Cl H SO₂ (Ph-2,5-Cl₂)2-CH₂CH₂CH₂-3 0 0 3779 Cl H SO₂ (Ph-2,5-Cl₂) 2,6-Me₂ 0 0 3780 Cl H SO₂(Ph-2,5-Cl₂) 2-Me, 6-cPr 0 0 3781 Cl H SO₂ (Ph-3-NO₂-4-Cl) 2-Me 0 0 3782Cl H SO₂ (Ph-3-NO₂-4-Cl) 2-iPr 0 0 3783 Cl H SO₂ (Ph-3-NO₂-4-Cl) 2-cPr 00 3784 Cl H SO₂ (Ph-3-NO₂-4-Cl) 2-CH₂CH₂CH₂-3 0 0 3785 Cl H SO₂(Ph-3-NO₂-4-Cl) 2,6-Me₂ 0 0 3786 Cl H SO₂ (Ph-3-NO₂-4-Cl) 2-Me, 6-cPr 00 3787 Cl H SO₂ (2-Thi) 2-Me 0 0 3788 Cl H SO₂ (2-Thi) 2-iPr 0 0 3789 ClH SO₂ (2-Thi) 2-cPr 0 0 3790 Cl H SO₂ (2-Thi) 2-CH₂CH₂CH₂-3 0 0 3791 ClH SO₂ (2-Thi) 2,6-Me₂ 0 0 3792 Cl H SO₂ (2-Thi) 2-Me, 6-cPr 0 0 3793 ClH N(Bu)₄ 2-Me 0 0 3794 Cl H N(Bu)₄ 2-iPr 0 0 3795 Cl H N(Bu)₄ 2-cPr 0 03796 Cl H N(Bu)₄ 2-CH₂CH₂CH₂-3 0 0 3797 Cl H N(Bu)₄ 2,6-Me₂ 0 0 3798 ClH N(Bu)₄ 2-Me, 6-cPr 0 0 3799 Cl H Li 2-Me, 6-cPr 0 0 3800 Cl H Na 2-Me0 0 3801 Cl H Na 2-iPr 0 0 3802 Cl H Na 2-cPr 0 0 3803 Cl H Na2CH₂CH₂CH₂-3 0 0 3804 Cl H Na 2,6-Me₂ 0 0 3805 Cl H Na 2-Me, 6-cPr 0 03806 Cl H K 2-Me 0 0 3807 Cl H K 2-iPr 0 0 3808 Cl H K 2-cPr 0 0 3809 ClH K 2-CH₂CH₂CH₂-3 0 0 3810 Cl H K 2,6-Me₂ 0 0 3811 Cl H K 2-Me, 6-cPr 00 3812 Cl H Rb 2-Me, 6-cPr 0 0 3813 Cl H Cs 2-Me, 6-cPr 0 0 3814 Cl H Mg2-Me, 6-cPr 0 0 3815 Cl H Ca 2-Me, 6-cPr 0 0 3816 Cl H Ba 2-Me, 6-cPr 00 3817 Cl H Sc 2-Me, 6-cPr 0 0 3818 Cl H Ti 2-Me, 6-cPr 0 0 3819 Cl H Mn2-Me, 6-cPr 0 0 3820 Cl H Fe 2-Me, 6-cPr 0 0 3821 Cl H Cu 2-Me, 6-cPr 00 3822 Cl H Ag 2-Me, 6-cPr 0 0 3823 Cl H Au 2-Me, 6-cPr 0 0 3824 Cl H Zn2-Me, 6-cPr 0 0 3825 Cl H Al 2-Me, 6-cPr 0 0 3826 Cl F H 2-Me 0 0 3827Cl F H 2-iPr 0 0 3828 Cl F H 2-cPr 0 0 3829 Cl F H 2-CH₂CH₂CH₂-3 0 03830 Cl F H 2,6-Me₂ 0 0 3831 Cl F H 2-Me, 6-cPr 0 0 3832 Cl Cl H 2-Me 00 3833 Cl Cl H 2-iPr 0 0 3834 Cl Cl H 2-cPr 0 0 3835 Cl Cl H2-CH₂CH₂CH₂-3 0 0 3836 Cl Cl H 2,6-Me₂ 0 0 3837 Cl Cl H 2-Me, 6-cPr 0 03838 Cl Br H 2-Me 0 0 3839 Cl Br H 2-iPr 0 0 3840 Cl Br H 2-cPr 0 0 3841Cl Br H 2-CH₂CH₂CH₂-3 0 0 3842 Cl Br H 2,6-Me₂ 0 0 3843 Cl Br H 2-Me,6-cPr 0 0 3844 Cl I H 2-Me 0 0 3845 Cl I H 2-iPr 0 0 3846 Cl I H 2-cPr 00 3847 Cl I H 2-CH₂CH₂CH₂-3 0 0 3848 Cl I H 2,6-Me₂ 0 0 3849 Cl I H2-Me, 6-cPr 0 0 3850 Cl H OCOPh 2-Me, 4-OCOPh 0 0 3851 Cl H CO-4-Thpy2-Me 0 0 3852 Cl H CO-4-Thpy 2-iPr 0 0 3853 Cl H CO-4-Thpy 2-cPr 0 03854 Cl H CO-4-Thpy 2-CH₂CH₂CH₂-3 0 0 3855 Cl H CO-4-Thpy 2,6-Me₂ 0 03856 Cl H CO-4-Thpy 2-Me, 6-cPr 0 0

Among the above-mentioned exemplary compounds, preferred compounds areCompounds Nos. 124, 125, 126, 127, 128, 130, 131, 132, 134, 136, 139,140, 144, 145, 151, 163, 173, 202, 207, 217, 226, 249, 264, 265, 266,267, 269, 270, 271, 272, 273, 279, 280, 284, 287, 292, 300, 304, 305,306, 307, 308, 309, 311, 330, 334, 336, 339, 344, 359, 361, 362, 364,365, 370, 377, 385, 386, 387, 390, 391, 400, 401, 403, 410, 412, 413,417, 422, 426, 437, 438, 441, 443, 446, 450, 456, 459, 472, 478, 498,505, 506, 507, 514, 515, 516, 521, 527, 528, 529, 531, 532, 534, 535,539, 541, 544, 547, 557, 562, 566, 571, 614, 618, 621, 623, 629, 640,642, 658, 659, 662, 663, 664, 667, 700, 701, 702, 704, 707, 708, 710,711, 712, 716, 717, 719, 728, 732, 733, 734, 735, 736, 737, 738, 740,756, 758, 759, 760, 761, 762, 775, 778, 780, 781, 782, 801, 802, 803,804, 805, 806, 827, 834, 844, 845, 846, 850, 890, 894, 896, 911, 914,931, 964, 965, 979, 982, 987, 998, 1000, 1007, 1009, 1013, 1016, 1020,1023, 1027, 1040, 1050, 1052, 1053, 1055, 1058, 1060, 1061, 1063, 1064,1066, 1069, 1073, 1083, 1086, 1088, 1089, 1091, 1096, 1099, 1100, 1102,1109, 1115, 1118, 1119, 1120, 1122, 1123, 1124, 1125, 1126, 1128, 1129,1133, 1140, 1151, 1160, 1172, 1178, 1184, 1207, 1251, 1260, 1266, 1286,1298, 1334, 1340, 1358, 1364, 1382, 1387, 1391, 1417, 1441, 1446, 1448,1456, 1459, 1461, 1481, 1509, 1522, 1531, 1537, 1543, 1549, 1553, 1554,1566, 1575, 1593, 1599, 1603, 1616, 1620, 1625, 1631, 1643, 1649, 1658,1706, 1710, 1757, 1770, 1789, 1811, 1840, 1877, 1879, 1891, 1898, 1911,1920, 1924, 1937, 1946, 1952, 1958, 1981, 1985, 2010, 2034, 2038, 2040,2042, 2051, 2060, 2066, 2072, 2081, 2106, 2136, 2147, 2151, 2176, 2198,2199, 2200, 2212, 2220, 2221, 2222, 2224, 2225, 2263, 2265, 2287, 2289,2300, 2309, 2315, 2321, 2327, 2333, 2411, 2431, 2453, 2519, 2529, 2540,2542, 2547, 2548, 2551, 2555, 2556, 2565, 2568, 2570, 2571, 2572, 2574,2576, 2577, 2585, 2587, 2589, 2592, 2596, 2597, 2599, 2600, 2601, 2603,2605, 2606, 2607, 2608, 2609, 2614, 2662, 2671, 2677, 2697, 2703, 2709,2715, 2721, 2727, 2733, 2739, 2746, 2752, 2758, 2764, 2770, 2776, 2782,2788, 2805, 2814, 2820, 2826, 2827, 2838, 2850, 2856, 2862, 2868, 2874,2880, 2900, 2906, 2918, 2924, 2930, 2961, 2970, 2976, 2982, 2988, 2994,3001, 3016, 3022, 3028, 3034, 3040, 3046, 3052, 3058, 3064, 3070, 3076,3082, 3088, 3094, 3100, 3106, 3112, 3129, 3138, 3144, 3150, 3156, 3162,3168, 3185, 3194, 3200, 3217, 3226, 3243, 3252, 3258, 3264, 3270, 3276,3282, 3288, 3294, 3300, 3306, 3312, 3318, 3324, 3330, 3336, 3342, 3348,3354, 3360, 3366, 3372, 3378, 3384, 3390, 3396, 3402, 3408, 3414, 3420,3426, 3432, 3438, 3444, 3450, 3456, 3462, 3468, 3474, 3480, 3486, 3492,3498, 3504, 3510, 3516, 3522, 3528, 3534, 3540, 3546, 3552, 3558, 3564,3570, 3576, 3582, 3588, 3594, 3600, 3606, 3612, 3618, 3624, 3630, 3636,3642, 3648, 3654, 3660, 3666, 3672, 3678, 3684, 3690, 3696, 3702, 3708,3714, 3720, 3755, 3780, 3786, 3792, 3798, 3805, 3811, 3837, 3843 or3849,

more preferably compounds of Compounds Nos. 124, 125, 126, 127, 128,130, 132, 136, 139, 140, 144, 145, 151, 163, 173, 202, 217, 249, 264,265, 266, 267, 269, 270, 271, 284, 287, 300, 304, 308, 309, 311, 334,336, 339, 361, 362, 377, 385, 386, 387, 390, 391, 401, 437, 438, 459,472, 505, 506, 507, 515, 516, 521, 528, 529, 531, 532, 534, 539, 541,544, 547, 571, 621, 658, 659, 662, 663, 664, 667, 700, 701, 702, 704,707, 708, 711, 712, 717, 719, 732, 733, 734, 735, 736, 737, 738, 740,756, 758, 759, 760, 762, 775, 778, 780, 781, 782, 801, 802, 803, 806,827, 834, 845, 846, 850, 896, 914, 931, 964, 965, 998, 1013, 1016, 1023,1040, 1050, 1052, 1053, 1055, 1058, 1060, 1061, 1063, 1064, 1066, 1069,1073, 1086, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1109, 1115, 1118,1119, 1120, 1123, 1124, 1125, 1126, 1129, 1133, 1140, 1151, 1160, 1172,1178, 1184, 1207, 1260, 1266, 1286, 1298, 1334, 1340, 1358, 1364, 1382,1387, 1391, 1417, 1441, 1446, 1448, 1481, 1522, 1531, 1537, 1543, 1549,1566, 1575, 1593, 1599, 1616, 1620, 1625, 1631, 1643, 1649, 1658, 1710,1770, 1789, 1811, 1840, 1879, 1891, 1911, 1937, 1946, 1958, 1981, 1985,2010, 2034, 2038, 2040, 2042, 2051, 2060, 2066, 2072, 2081, 2106, 2136,2151, 2176, 2200, 2212, 2220, 2225, 2265, 2289, 2300, 2309, 2327, 2333,2411, 2519, 2529, 2540, 2542, 2556, 2565, 2568, 2576, 2577, 2587, 2597,2599, 2600, 2601, 2605, 2609, 2614, 2662, 2671, 2677, 2697, 2703, 2709,2715, 2721, 2727, 2733, 2739, 2746, 2752, 2758, 2764, 2770, 2776, 2782,2788, 2805, 2814, 2820, 2826, 2850, 2856, 2862, 2868, 2874, 2880, 2900,2906, 2918, 2924, 2930, 2961, 2970, 2976, 2982, 2988, 2994, 3022, 3028,3034, 3040, 3046, 3052, 3058, 3064, 3070, 3076, 3082, 3088, 3094, 3100,3106, 3112, 3129, 3138, 3144, 3162, 3168, 3185, 3194, 3200, 3217, 3226,3243, 3252, 3258, 3264, 3270, 3276, 3282, 3288, 3294, 3300, 3306, 3312,3318, 3324, 3330, 3336, 3342, 3348, 3354, 3360, 3366, 3372, 3378, 3384,3390, 3396, 3402, 3408, 3414, 3420, 3426, 3432, 3438, 3444, 3450, 3456,3462, 3468, 3474, 3480, 3486, 3492, 3498, 3504, 3510, 3516, 3528, 3534,3540, 3546, 3552, 3558, 3564, 3570, 3576, 3582, 3588, 3594, 3600, 3606,3612, 3618, 3624, 3630, 3636, 3642, 3648, 3654, 3660, 3666, 3672, 3678,3684, 3690, 3696, 3702, 3708, 3714, 3720, 3755, 3780, 3786, 3792, 3798,3805, 3811, 3837, 3843 or 3849,

still further preferably compounds of Compounds Nos. 125, 126, 127, 128,130, 132, 139, 140, 144, 145, 151, 163, 217, 249, 264, 265, 266, 284,304, 308, 387, 390, 391, 459, 472, 506, 507, 515, 516, 531, 539, 541,621, 658, 659, 662, 700, 701, 702, 704, 711, 717, 719, 733, 734, 735,740, 758, 759, 762, 775, 780, 781, 801, 802, 803, 806, 827, 834, 846,850, 931, 964, 965, 1023, 1040, 1050, 1052, 1053, 1055, 1058, 1061,1064, 1066, 1069, 1073, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1109,1119, 1124, 1125, 1126, 1129, 1133, 1151, 1160, 1172, 1178, 1184, 1207,1260, 1286, 1298, 1334, 1340, 1358, 1382, 1417, 1441, 1481, 1522, 1531,1537, 1543, 1549, 1566, 1593, 1599, 1616, 1625, 1631, 1643, 1649, 1770,1811, 1891, 1958, 2034, 2051, 2060, 2072, 2136, 2176, 2212, 2265, 2309,2327, 2333, 2519, 2556, 2577, 2587, 2597, 2599, 2600, 2601, 2609, 2614,2662, 2677, 2697, 2709, 2715, 2721, 2727, 2733, 2739, 2746, 2752, 2758,2764, 2770, 2776, 2782, 2788, 2805, 2814, 2820, 2826, 2850, 2862, 2868,2874, 2900, 2918, 2924, 2930, 2961, 2970, 2988, 2994, 3022, 3034, 3046,3058, 3064, 3076, 3082, 3094, 3106, 3112, 3129, 3144, 3162, 3168, 3185,3217, 3243, 3252, 3264, 3282, 3288, 3294, 3306, 3324, 3330, 3336, 3354,3378, 3390, 3396, 3402, 3408, 3414, 3420, 3426, 3432, 3438, 3450, 3462,3468, 3474, 3486, 3492, 3510, 3516, 3546, 3552, 3564, 3582, 3588, 3594,3600, 3606, 3612, 3618, 3624, 3642, 3654, 3660, 3678, 3690, 3696, 3702,3780, 3786, 3798, 3805, 3811, 3837, 3843 or 3849,

particularly preferably compounds of Compounds Nos. 127, 128, 132, 139,144, 217, 265, 284, 304, 391, 472, 506, 507, 515, 516, 539, 541, 621,658, 659, 662, 704, 711, 717, 719, 733, 735, 740, 758, 759, 762, 780,781, 801, 802, 803, 806, 827, 846, 850, 931, 964, 965, 1023, 1040, 1052,1058, 1061, 1088, 1089, 1091, 1096, 1099, 1100, 1102, 1109, 1124, 1125,1151, 1160, 1172, 1184, 1207, 1286, 1298, 1334, 1358, 1417, 1441, 1481,1522, 1531, 1537, 1543, 1566, 1593, 1599, 1616, 1625, 1631, 1643, 1770,1811, 1891, 1958, 2034, 2051, 2176, 2212, 2265, 2309, 2327, 2333, 2597,2599, 2614, 2662, 2677, 2727, 2733, 2739, 2746, 2752, 2805, 2814, 2850,2900, 2918, 2961, 2994, 3022, 3046, 3064, 3094, 3129, 3144, 3168, 3185,3217, 3243, 3264, 3288, 3402, 3408, 3426, 3432, 3450, 3462, 3546, 3552,3564, 3582, 3588, 3594, 3600, 3606, 3612, 3618, 3624, 3642, 3654, 3660,3678, 3690, 3696, 3702, 3805 or 3811,

most preferably compounds of 6-chloro-3-(2-methylphenoxy)-4-pyridazinol(Compound No. 128), 6-chloro-3-(2-isopropylphenoxy)-4-pyridazinol(Compound No. 132), 6-chloro-3-(2-cyclopropylphenoxy)-4-pyridazinol(Compound No. 139),6-chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]-4-pyridazinol (CompoundNo. 265), 6-chloro-3-(2,3-dihydro-1H-inden-4-yloxy)-4-pyridazinol(Compound No. 506),6-chloro-3-(2-cyclopropyl-5-methylphenoxy)-4-pyridazinol (Compound No.662), 6-chloro-3-(2-fluoro-6-isopropylphenoxy)-4-pyridazinol (CompoundNo. 717), 6-chloro-3-(2-chloro-6-cyclopropylphenoxy)-4-pyridazinol(Compound No. 740), 6-chloro-3-(2,6-dimethylphenoxy)-4-pyridazinol(Compound No. 801),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (Compound No.806),6-chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]-4-pyridazinol(Compound No. 827),6-chloro-3-(2-cyclopropyl-3,5-dimethylphenoxy)-4-pyridazinol (CompoundNo. 1023),6-chloro-3-(6-cyclopropyl-3-fluoro-2-methylphenoxy)-4-pyridazinol(Compound No. 1052),6-chloro-3-(6-cyclopropyl-2,3-dimethylphenoxy)-4-pyridazinol (CompoundNo. 1061), 6-chloro-3-(2,3,5,6-tetramethylphenoxy)-4-pyridazinol(Compound No. 1125),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl acetate(Compound No. 1151),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl propionate(Compound No. 1160),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methylpropanoate (Compound No. 1172),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl pivalate(Compound No. 1207),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-methyl-2-butenoate (Compound No. 1358),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl benzoate(Compound No. 1417),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methylbenzoate (Compound No. 1481),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methoxybenzoate (Compound No. 1522),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-methylbenzoate (Compound No. 1531),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-bromobenzoate(Compound No. 1543),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methylbenzoate (Compound No. 1566),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl phthalate (CompoundNo. 1625), 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl isophthalate(Compound No. 1631),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylisobutylcarbonate (Compound No. 1770),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldimethylcarbamate (Compound No. 1891),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-propanesulfonate (Compound No. 2051),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl benzenesulfonate (Compound No. 2176),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-chlorobenzenesulfonate (Compound No. 2212),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2265),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methoxybenzene sulfonate (Compound No. 2309),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazoyl-5-yl 1,2-benzenedisulfonate (Compound No. 2327),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl 1,3-benzenedisulfonate (Compound No. 2333),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,3-dimethylbutanoate (Compound No. 2662),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl ethyl succinate(Compound No. 2727),bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl] succinate(Compound No. 2733),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl pentanedioate(Compound No. 2739),bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]pentanedioate (Compound No. 2746),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 2-bromobenzoate(Compound No. 2805),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl 4-ethylbenzoate(Compound No. 2961),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,5-dimethylbenzoate (Compound No. 3129),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-fluoro-4-methylbenzoate (Compound No. 3185),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,5-difluorobenzoate (Compound No. 3217),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,5-dimethylbenzoate (Compound No. 3243),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethoxy(methyl)carbamate (Compound No. 3564),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbis(2-methoxyethyl)carbamate (Compound No. 3600),6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-azetizincarboxylate (Compound No. 3612) or6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-morpholinecarboxylate (Compound No. 3690).

The 3-phenoxy-4-pyridazinol compound and its ester derivative of thepresent invention can be produced by the methods described in thefollowing Steps A to N.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the samemeanings as defined in the above, L represents a leaving group, and forexample, it may be a halogen atom, a C₁ to C₆ alkylsulfonyloxy group ora phenylsulfonyloxy group (the phenylsulfonyloxy group may besubstituted by the same or different 1 to 5 halogen atom(s) or C₁ to C₆alkyl group(s).),

-   X repersents a hydrogen atom or an acyl group,-   Y represents, in addition to X, other protective groups for the    hydroxyl group, and for example, it may be a methyl group, a    methoxymethyl group, a methoxyethoxymethyl group or a benzyl group.

Step A is a step to produce Compound (Ia) of the present invention or acompound represented by the formula (VII), in which a hydroxyl group isprotected, by reacting a phenol compound represented by the formula(III) with a pyridazine compound represented by the formula (II), then,chlorinating the resulting compound, and futher reacting an oxygennucleophilic agent, and further a step to produce Compound (Ib) of thepresent invention by removing the protective group of Compound (VII).

(Step A-1)

Step A-1 is a step to produce a phenoxypyridazine compound representedby the formula (IV) by reacting Compound (II) with Compound (III) in thepresence or absence of a solvent, and if necessary, in the presence of abase.

The base to be used is not specifically limited so long as it is a baseshowing generally a pH of 8 or more, and for example, it may be alkalimetal hydroxides such as sodium hydroxide, potassium hydroxide, etc.;alkali metal carbonates such as sodium carbonate, potassium carbonate,cesium carbonate, etc.; metal alkoxides such as sodium methoxide, sodiumethoxide, potassium t-butoxide, etc.; alkali metal hydrides such assodium hydride, potassium hydride, etc.; alkali metals such as sodium,potassium, etc.; aliphatic tertiary amines such as triethylamine,tributylamine, diisopropylethylamine, etc.; aliphatic cyclic tertiaryamines such as 1,4-diazabicyclo[2.2.2]-octane (DABCO),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), etc.; pyridines such aspyridine, collidine, 4-(N,N-dimethylamino)pyridine, etc.; organic metalbases such as n-butyl lithiums, s-butyl lithium, lithiumdiisopropylamide, sodium bis(trimehylsilyl)amide, lithiumbis(trimethylsilyl)amide, etc., preferably alkali metal hydroxides,alkali metal carbonates, metal alkoxides, alkali metal hydrides oralkali metals, more preferably potassium carbonate, potassiumt-butoxide, sodium hydride or sodium.

An amount of the base to be used is generally 0.5 to 5 mol, preferably 1to 3 mol based on 1 mol of the compound (II).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be water; alcohols such asmethanol, ethanol, t-butanol, etc.; ketones such as acetone, methylisobutyl ketone, etc.; nitriles such as acetonitrile, etc.; esters suchas ethyl acetate, etc.; halogenated hydrocarbons such as methylenechloride, chloroform, dichloroethane, etc.; ethers such as diethylether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such astoluene, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; or a mixed solvent ofthe above, preferably nitriles, halogenated hdyrocarbons, ethers,aromatic hydrocarbons, amides or sulfoxides, more preferably dioxane,toluene, dimethylformamide or dimethylsulfoxide.

The reaction temperature may vary depending on the starting compounds,reaction reagents and solvent, etc., and is generally −90° C. to 200°C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 48 hours, preferably 15 minutes to 12hours.

(Step A-2)

Step A-2 is a step to producing a compound represented by the formula(V) in which a chlorine atom is introduced into the 4-position of apyridazine ring by chlorinating Compound (IV) with a chlorinating agentin the presence or absence of a solvent.

As the chlorinating agent to be used, it is not specifically limited solong as it can chlorinate an aromatic ring, and for example, it may bechlorine, chlorine-iron chloride, sulfuryl chloride, copper chloride,N-chlorosuccinimide or phosphorus pentachloride, preferably chlorine.

An amount of the chlorinating agent to be used is generally 0.5 to 10mol, preferably 1 to 2 mol based on 1 mol of the compound (IV).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be phosphorus oxychloride;water; alcohols such as methanol, ethanol, t-butanol, etc.; halogenatedhydrocarbons such as methylene chloride, chloroform, dichloroethane,etc.; ethers such as diethyl ether, tetrahydrofuran, dioxane, etc.;aromatic hydrocarbons such as toluene, etc.; amides such asdimethylformamide, dimethylacetamide, etc.; sulfoxides such asdimethylsulfoxide, etc.; aliphatic hydrocarbons such as hexane,cyclohexane, heptane, etc.; or a mixed solvent of the above, preferablyphosphorus oxychloride, water, halogenated hdyrocarbons or ethers, morepreferably phosphorus oxychloride.

The reaction temperature may vary depending on the starting compounds,reaction reagents and a kind of the solvent to be used, etc., and isgenerally −90° C. to 200° C., preferably 0° C. to 50° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 24 hours, preferably 15 minutes to 6hours.

(Step A-3)

Step A-3 is a step to produce Compound (Ia) of the present invention ora compound represented by the formula (VII), in which a hydroxyl groupis protected, by reacting Compound (V) with an oxygen nucleophilic agentrepresented by the formula (VI) in the presence or absence of a solvent,and if necessary, in the presence of a base.

The base to be used is not specifically limited so long as it is a baseshowing generally a pH of 8 or more, and for example, it may be alkalimetal hydroxides such as sodium hydroxide, potassium hydroxide, etc.;alkali metal carbonates such as sodium carbonate, potassium carbonate,cesium carbonate, etc.; metal alkoxides such as sodium methoxide, sodiumethoxide, potassium t-butoxide, etc.; alkali metal salts of an organicacid such as sodium acetate, potassium acetate, sodium formate,potassium formate, etc.; alkali metal hydrides such as sodium hydride,potassium hydride, etc.; alkali metals such as sodium, potassium, etc.;aliphatic tertiary amines such as triethylamine, tributylamine,diisopropylethylamine, etc.; aliphatic cyclic tertiary amines such as1,4-diazabicyclo-[2.2.2]octane (DABCO),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), etc.; pyridines such aspyridine, collidine, 4-(N,N-dimethylamino)pyridine, etc.; organic metalbases such as n-butyl lithiums, s-butyl lithium, lithiumdiisopropylamide, sodium bis(trimehylsilyl)amide, lithiumbis(trimethylsilyl)amide, etc., preferably alkali metal hydroxides,alkali metal carbonates, metal alkoxide, alkali metal salts of anorganic acid, alkali metal hydrides or alkali metals, more preferablysodium hydroxide, potassium hydroxide, potassium carbonate, potassiumt-butoxide, sodium acetate, sodium formate, sodium hydride or sodium.

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, for example, water; alcohols such as methanol, ethanol,t-butanol, etc.; ketones such as acetone, methyl isobutyl ketone, etc.;nitriles such as acetonitrile, etc.; esters such as ethyl acetate, etc.;halogenated hydrocarbons such as methylene chloride, chloroform,dichloroethane, etc.; ethers such as diethyl ether, tetrahydrofuran,dioxane, etc.; aromatic hydrocarbons such as toluene, etc.; amides suchas dimethylformamide, dimethylacetamide, etc.; sulfoxides such asdimethylsulfoxide, etc.; or a mixed solvent of the above, preferablywater, alcohols, nitriles, ethers, amides or sulfoxides, more preferablywater, methanol, acetonitrile, tetrahydrofuran, dioxane,dimethylformamide or dimethylsulfoxide.

The reaction temperature may vary depending on the starting compounds,reaction reagents and a kind of the solvent to be used, etc., and isgenerally −90° C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and is usually 5 minutes to 24 hours, preferably 15 minutes to 6hours.

Incidentally, in the present step, the compound (VI) may be used in thepresent step after making a salt by previously reacting with a base.

(Step A-4)

Step A-4 is a step to produce Compound (Ib) of the present invention byremoving the protective group for a hydroxyl group of Compound (VII).

The protective group to be used in the present step is not specificallylimited so long as it can selectively removed from Compound (VII) toprovide Compound (Ib), and for example, it may be a methyl group,methoxymethyl group, benzyloxymethyl group, methoxyethoxymethyl group,2-(trimethylsilyl)ethoxymethyl group, methylthiomethyl group,phenylthiomethyl group, 2,2-dichloro-1,1-difluoroethyl group,tetrahydropyranyl group, phenacyl group, p-bromophenacyl group,cyclopropylmethyl group, allyl group, isopropyl group, cyclohexyl group,t-butyl group, benzyl group, 2,6-dimethylbenzyl group, 4-methoxybenzylgroup, 2-nitrobenzyl group, 2,6-dichlorobenzyl group,4-(dimethylaminocarbonyl)benzyl group, 9-anthrylmethyl group, 4-picolylgroup, heptafluoro-p-tolyl group or tetrafluoro-4-pyridyl group,preferably a methyl group, methoxymethyl group, methoxyethoxymethylgroup, methylthiomethyl group, tetrahydropyranyl group, phenacyl group,allyl group or benzyl group, more preferably a methyl group.

A method for removing the protective group to be used in the presentstep is not specifically limited so long as it can selectively removethe protective group for a hydroxyl group, and it can be carried out bythe conventionally known method (for example, a method described inProtective Groups in Organic Synthesis, 13^(th) Edition, written byTheodora W. Greene and Peter G. M. Wuts, JOHN WILEY & SONS, INC.) withregard to the respective protecttive groups or in accordance with thesemethods. For example, when the protective group is a methyl group,removal of the methyl group can be carried out, for example, by reactingwith a potassium salt or sodium salt of 2-hydroxypyridine indimethylsulfoxide, a sodium salt of ethanethiol in dimethylformamide, orboron tribromide in methylene chloride. For example, when the protectivegroup is a methoxymethyl group, removal of the methoxymethyl group canbe carried out, for example, by reacting with trifluoroacetic acid. Forexample, when the protective group is a methoxyethoxymethyl group,removal of the methoxyethoxymethyl group can be carried out, forexample, by reacting with trifluoroacetic acid. Also, for example, whenthe protective group is a benzyl group, removal of the benzyl group canbe carried out by catalytic hydrogenation.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, L, X and Y have thesame meanings as defined in the above.

Step B is a step to produce Compound (Ia) of the present invention or acompound represented by the formula (VII), in which a hydroxyl group isprotected, by oxidizing a pyridazine compound represented by the formula(II), reacting a phenol compound represented by the formula (III) to theresulting compound, then chlorinating the resulting compound, andfurther reacting an oxygen nucleophilic agent, or a step to produceCompound (Ib) of the present invention by removing the protective groupof Compound (VII).

(Step B-1)

Step B-1 is a step to produce Pyridazine N-oxide represented by theformula (VIII) by oxidizing Compound (II) with an oxidizing agent in thepresence or absence of a solvent.

The oxidizing agent to be used is not specifically limited so long as itcan convert an amine into an N-oxide, and for example, it may beperoxides such as m-chloroperbenzoic acid (mcpba), peracetic acid,pertrifluoroacetic acid, trifluoroacetic anhydride-hydrogen peroxide,peroxydichloromaleic acid, dichloromaleic acid-hydrogen peroxide,peroxymaleic acid, maleic acid-hydrogen peroxide, t-butylhydroperoxide,t-butylhydroperoxide-vanadium oxyacetylacetonate,t-butylhydroperoxide-molybdenum chloride, hydrogen peroxide, etc.;ozone; or oxygen, preferably m-chloroperbenzoic acid (mcpba),trifluoroacetic anhydride-hydrogen peroxide or dichloromaleicacid-hydrogen peroxide.

An amount of the oxidizing agent to be used in the reaction is usually0.5 to 100 mol, preferably 1 to 2 mol based on 1 mol of Compound (II).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be water; alcohols such asmethanol, ethanol, t-butanol, etc.; ketones such as acetone, methylisobutyl ketone, etc.; nitriles such as acetonitrile, etc.; esters suchas ethyl acetate, etc.; halogenated hydrocarbons such as methylenechloride, chloroform, dichloroethane, etc.; ethers such as diethylether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such astoluene, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; or a mixed solvent ofthe above, preferably halogenated hdyrocarbons, more preferablymethylene chloride.

The reaction temperature may vary depending on the starting compounds,reaction reagents and solvents, etc., and is generally −90° C. to 200°C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 24 hours, preferably 15 minutes to 6hours.

According to the present step, an isomer in which other nitrogen atom isoxidized may be by-produced in some cases, and an objective PyridazineN-oxide can be obtained by purifying the resulting materials aftercompletion of the present step, or carrying out the subsequent steps ina state of admixture and by purifying the resulting materials aftercompletion of the step.

(Step B-2)

Step B-2 is a step to produce a phenoxypyridazine compound representedby the formula (IX) by reacting Compound (VIII) with Compound (III) inthe presence or absence of a solvent, and if necessary, in the presenceof a base.

The present step can be carried out in accordance with Step A-1.

(Step B-3)

Step B-3 is a step to produce Compound (V) by reacting Compound (IX)with phosphorus oxychloride in the presence or absence of a solvent.

An amount of the phosphorus oxychloride to be used in the present stepis generally 0.5 to 100 mol, preferably 1 to 5 mol based on 1 mol ofCompound (IX).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be ketones such as acetone,methyl isobutyl ketone, etc.; nitriles such as acetonitrile, etc.;esters such as ethyl acetate, etc.; halogenated hydrocarbons such asmethylene chloride, chloroform, dichloroethane, etc.; ethers such asdiethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbonssuch as toluene, etc.; amides such as dimethylformamide,dimethylacetamide, etc.; sulfoxides such as dimethylsulfoxide, etc.;aliphatic hydrocarbons such as hexane, cyclohexane, etc.; or a mixedsolvent of the above, preferably halogenated hdyrocarbons, morepreferably methylene chloride or chloroform.

The reaction temperature may vary depending on the starting compounds,reaction reagents and solvents, etc., and is generally −90° C. to 200°C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 72 hours, preferably 30 minutes to 24hours.

(Step B-4)

Step B-4 is a step to produce Compound (Ia) of the present invention ora compound represented by the formula (VII), in which a hydroxyl groupis protected, by reacting Compound (V) with an oxygen nucleophilic agentrepresented by the formula (VI) in the presence or absence of a solvent,and if necessary, in the presence of a base.

The present step is similar to Step A-3.

(Step B-5)

Step B-5 is a step to produce Compound (Ib) of the present invention byremoving the protective group for a hydroxyl group of Compound (VII).

The present step is similar to Step A-4.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, X and Y have the samemeanings as defined in the above.

Step C is a step to produce Compound (Ia) of the present invention or acompound represented by the formula (VII), in which a hydroxyl group isprotected, by oxidizing Compound (IV), then chlorinating the resultingmaterial, and then reacting the same with an oxygen nucleophilic agent,and further a step to produce Compound (Ib) of the present invention byremoving the protective group of Compound (VII).

(Step C-1)

Step C-1 is a step to produce Pyridazine N-oxide represented by theformula (IX) by oxidizing Compound (IV) with an oxidizing agent in thepresence or absence of a solvent.

The present step can be carried out in accordance with Step B-1.

(Step C-2)

Step C-2 is a step to produce Compound (V) by reacting Compound (IX)with phosphorus oxychloride in the presence or absence of a solvent.

The present step is similar to Step B-3.

(Step C-3)

Step C-3 is a step to produce Compound (Ia) of the present invention ora compound represented by the formula (VII), in which a hydroxyl groupis protected, by reacting Compound (V) with an oxygen nucleophilic agentrepresented by the formula (VI) in the presence or absence of a solvent,and if necessary, in the presence of a base.

The present step is similar to Step A-3 or B-4.

(Step C-4)

Step C-4 is a step to produce Compound (Ib) of the present invention byremoving the protective group for a hydroxyl group of Compound (VII).

The present step is similar to Step A-4 or B-5.

In the above formula, R¹, R², R³, R⁴, R⁵, R^(6, R) ⁷, L, X and Y havethe same meanings as defined above.

Step D is a step to produce Compound (Ia) of the present invention or acompound represented by the formula (VII), in which a hydroxyl group isprotected, by reacting a pyridazine compound represented by the formula(X), into which an oxygen functional group has previously beensubstituted, with a phenol represented by the formula (III), and furthera step to produce Compound (Ib) of the present invention by removing theprotective group of Compound (VII).

(Step D-1)

Step D-1 is a step to produce Compound (Ia) of the present invention ora compound represented by the formula (VII), in which a hydroxyl groupis protected, by reacting Compound (X) with Compound (III) in thepresence or absence of a solvent, and if necessary, in the presence of abase.

The present step can be carried out in accordance with Step A-1 or B-2.

(Step D-2)

Step D-2 is a step to produce Compound (Ib) of the present invention byremoving the protective group for a hydroxyl group for Compound (VII).

The present step is similar to Step A-4, B-5 or C-4.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, L, X and Y have thesame meanings as defined above, m′ and n′ each represent 0 or 1,provided that m′ and n′ are not simultaneously 0.

Step E is a step to produce Compound (Ic) of the present invention or acompound represented by the formula (XII), in which a hydroxyl group isprotected, by oxidizing a pyridazine compound to which an oxygenfunctional group has previously been substituted represented by theformula (X), and then reacting a phenol represented by the formula(III), and further a step to produce Compound (Id) of the presentinvention by removing the protective group of Compound (XII).

(Step E-1)

Step E-1 is a step to produce Pyridazine N-oxide represented by theformula (XI) by oxidizing Compound (X) with an oxidizing agent in thepresence or absence of a solvent.

The present step can be carried out in accordance with Step B-1 or C-1in the case where m′=0 or n′=0, and when m′=n′=1, it can be carried outunder severer conditions by making an amount of the oxidizing agent inexcessive, by using an oxidizing agent having higher reactivity to carryout the oxidation, and the like.

(Step E-2)

Step E-2 is a step to produce Compound (Ic) of the present invention ora compound represented by the formula (XII), in which a hydroxyl groupis protected, by reacting Compound (XI) with Compound (III) in thepresence or absence of a solvent, and if necessary, in the presence of abase.

The present step can be carried out in accordance with Step A-1, B-2 orD-1.

(Step E-3)

Step E-3 is a step to produce Compound (Id) of the present invention byremoving the protective group for a hydroxyl group of Compound (XII).

The present step is similar to Step A-4, B-5, C-4 or D-2.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, X, Y, m′ and n′ havethe same meanings as defined above.

Step F is a step to produce Compound (Ic) of the present invention or acompound represented by the formula (XII), in which a hydroxyl group isprotected, by oxidizing Compound (Ia) of the present invention or acompound represented by the formula (VII) in which a hydroxyl group isprotected, and further is a step to produce Compound (Id) of the presentinvention by removing the protective group of Compound (XII).

(Step F-1)

Step F-1 is a step to produce Compound (Ic) of the present invention ora compound represented by the formula (XII), in which a hydroxyl groupis protected, by oxidizing Compound (Ia) of the present invention orCompound (VII) with an oxidizing agent in the presence or absence of asolvent.

The present step can be carried out in accordance with Step E-1.

(Step F-2)

Step F-2 is a step to produce Compound (Id) of the present invention byremoving the protective group for a hydroxyl group of Compound (XII).

The present step is similar to Step A-4, B-5, C-4, D-2 or E-3.

In the above formula, R¹, R³, R⁴, R⁵, R⁶, R⁷, X and Y have the samemeanings as defined above, R^(2a) has the same meaning as R² except forremoving a hydrogen atom.

Step G is a step to produce Compound (If) of the present invention or acompound represented by the formula (XIV), in which a hydroxyl group isprotected, by subjecting the 5-position of the pyridazine ring ofCompound (Ie) of the present invention or a compound represented by theformula (XIII), in which a hydroxyl group is protected, to metalation,and then reacting an electrophilic agent to the resulting material, andfurther is a step to produce Compound (Ig) of the present invention byremoving the protective group of Compound (XIV).

(Step G-1)

Step G-1 is a step to produce Compound (If) of the present invention ora compound represented by the formula (XIV), in which a hydroxyl groupis protected, by reacting Compound (Ie) of the present invention or acompound represented by the formula (XIII), in which a hydroxyl group isprotected, with a metalating agent in the presence or absence of asolvent, and then, reacting with an electrophilic agent.

The metalating agent to be used is not specifically limited so long asit can metalate an aromatic ring, and for example, it may be organiclithium compounds such as methyl lithium, butyl lithium, s-butyllithium, t-butyl lithium, phenyl lithium, etc.; organic magnesiumcompounds such as methylmagnesium chloride, methyl magnesium bromide,ethyl magnesium bromide, phenylmagnesium bromide, etc.; organometalamides such as lithium diisopropylamide, sodiumbis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, etc.; metalalkoxides such as sodium methoxide, sodium ethoxide, potassiumt-butoxide, etc.; alkali metal hydrides such as sodium hydride,potassium hydride, etc.; alkali metals such as lithium, sodium,potassium, etc.; alkaline earth metals such as magnesium, etc.,preferably organic lithium compounds, more preferably butyl lithium.

An amount of the metalating agent to be used in the reaction isgenerally 0.5 to 10 mol, preferably 1 to 2 mol based on 1 mol ofCompound (Ie) or Compound (XIII).

The electrophilic agent to be used in the reaction is not specificallylimited so long as it can be a nucleophilic agent capable of reactingwith an organometallic compound, and for example, it may be silylatingagents such as trimethylsilyl chloride, triethylsilyl chloride,t-butyldimethylsilyl chloride, trimethylsilyl trifluoromethanesulfonate, etc.; acylating agents such as acetyl chloride, benzoylchloride, ethyl chlorocarbonate, methyl chlorocarbonate,N,N-dimethylformamide, methyl formate, etc.; carbonyl compounds such asacetaldehyde, benzaldehyde, acetone, cyclohexanone, etc.; alkylatingagents such as methyl iodide, methyl bromide, benzyl bromide, etc.;halogenating agents such as fluorine, chlorine, bromine, iodine,N-fluorobenzene sulfonamide, 1-fluoro-2,6-dichloropyridinium triflate,N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS), etc.; or carbondioxide, preferably a silylating agent, acylating agent, alkylatingagent or halogenating agent, more preferably trimethylsilyl chloride,benzoyl chloride, ethyl chlorocarbonate or methyl iodide.

An amount of the electrophilic agent to be used in the reaction isgenerally 0.5 to 10 mol, preferably 1 to 3 mol based on 1 mol ofCompound (Ie) or Compound (XIII).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be halogenated hydrocarbons suchas methylene chloride, chloroform, dichloroethane, etc.; ethers such asdiethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbonssuch as toluene, etc.; aliphatic hydrocarbons such as hexane,cyclohexane, etc.; or a mixed solvent of the above, preferably ethers,more preferably tetrahydrofuran.

The reaction temperature may vary depending on starting materials,reaction reagents and a kind of the solvent to be used, etc., andusually −90° C. to 100° C., preferably −70° C. to 30° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 24 hours, preferably 30 minutes to 12hours.

(Step G-2)

Step G-2 is a step to produce Compound (Ig) of the present invention byremoving the protective group for a hydroxyl group of Compound (XIV).

The present step is similar to Step A-4, B-5, C-4, D-2, E-3 or F-2.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the samemeanings as defined above,

-   X^(a) represents the same meanings as X except for removing a    hydrogen atom.

Step H is a step to convert an ester derivative represented by theformula (Ih) of the present invention into a hydroxy compoundrepresented by the formula (Ib) of the present invention.

(Step H-1)

Step H-1 is a step to produce Compound (Ib) of the present invention byreacting Compound (Ih) of the present invention with a nucleophilicagent in the presence or absence of a solvent.

The nucleophilic agent to be used is not specifically limited so long asit can nucleophilically attack an ester derivative, and cleave the esterbonding to an acid portion and an alcohol portion, and for example, itmay be water; hydroxides of an alkali metal such as lithium hydroxide,sodium hydroxide, potassium hydroxide, etc.; hydroxides of an alkalineearth metal such as magnesium hydroxide, calcium hydroxide, etc.; metalalkoxides such as sodium methoxide, sodium ethoxide, 2-hydroxypyridinepotassium salt, 2-hydroxypyridine sodium salt, etc.; alkali metal saltsof an organic acid such as sodium acetate, potassium acetate, sodiumformate, potassium formate, etc.; fluorides such as tetrabutylammoniumfluoride, potassium fluoride, etc.; chlorides such as lithium chloride,sodium chloride, etc.; bromides such as lithium bromide, sodium bromide,etc.; iodides such as sodium iodide, potassium iodide, etc.; or metalsalts of a sulfur compound such as methanethiol sodium salt, ethanethiolsodium salt, etc., preferably water, hydroxides of an alkali metal,metal alkoxides or alkali metal salts of an organic acid, morepreferably water, sodium hydroxide, potassium hydroxide or sodiumacetate.

An amount of the nucleophilic agent to be used is generally 1 to 10 mol,preferably 1 to 5 mol based on 1 mol of Compound (Ih).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be water; alcohols such asmethanol, ethanol, t-butanol, etc.; ketones such as acetone, methylisobutyl ketone, etc.; nitrites such as acetonitrile, etc.; esters suchas ethyl acetate, etc.; halogenated hydrocarbons such as methylenechloride, chloroform, dichloroethane, etc.; ethers such as diethylether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such astoluene, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; or a mixed solvent ofthe above, preferably water, alcohols, nitrites, ethers, amides orsulfoxides, more preferably water, methanol, ethanol, tetrahydrofuran,dioxane, dimethylformamide or dimethylsulfoxide.

The reaction temperature may vary depending on starting materials,reaction reagents and a kind of the solvent to be used, etc., andusually −90° C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 48 hours, preferably 15 minutes to 12hours.

Incidentally, in the present step, a conventionally known method can beemployed as usual deprotection of a hydroxyl group.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and X^(a) have the samemeanings as defined above.

Step I is a step to convert the hydroxy compound represented by theformula (Ib) of the present invention tinot an ester derivativerepresented by the formula (Ih) of the present invention.

(Step I-1)

Step I-1 is a step to produce Compound (Ih) of the present invention byreacting Compound (Ib) of the present invention with an esterifyng agentin the presence or absence of a solvent.

The esterifying agent to be used is not specifically limited so long asit can esterify a hydroxyl group, and for example, it may be acylatingagents such as acetyl chloride, acetyl bromide, acetic anhydride,trifluoroacetic anhydride, benzoyl chloride, methyl chlorocarbonate,ethyl chlorocarbonate, N,N-dimethylcarbamoyl chloride, methylchlorothioformate, etc.; or sulfonylating agents such as methanesulfonylchloride, propanesulfonyl chloride, p-toluenesulfonyl chloride,trifluoromethanesulfonic acid anhydride, N,N-dimethylsulfamoyl chloride,etc., preferably acetyl chloride, acetic anhydride, trifluoroaceticanhydride, benzoyl chloride, methyl chlorocarbonate, ethylchlorocarbonate, methanesulfonyl chloride, propanesulfonyl chloride,p-toluenesulfonyl chloride or trifluoromethanesulfonic acid anhydride,more preferably benzoyl chloride, p-toluenesulfonyl chloride ortrifluoromethanesulfonic acid anhydride.

An amount of the esterifying agent to be used in the reaction isgenerally 0.5 to 10 mols, preferably 1 to 3 mols based on 1 mol ofCompound (Ib).

The reaction is preferably carried out in the presence of a base.

The base to be used is not specifically limited so long as it is a baseshowing a pH of 8 or more, and for example, it may be alkali metalhydroxides such as sodium hydroxide, potassium hydroxide, etc.; alkalimetal carbonates such as sodium carbonate, potassium carbonate, cesiumcarbonate, etc.; metal alkoxides such as sodium methoxide, sodiumethoxide, potassium t-butoxide, etc.; alkali metal hydrides such assodium hydride, potassium hydride, etc.; aliphatic tertiary amines suchas triethylamine, tributylamine, diisopropylethylamine, etc.; aliphaticcyclic tertiary amines such as 1,4-diazabicyclo-[2.2.2]octane (DABCO),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), etc.; pyridines such aspyridine, collidine, 4-(N,N-dimethylamino)pyridine, etc.; or organicmetal bases such as n-butyl lithiums, s-butyl lithium, lithiumdiisopropylamide, sodium bis(trimehylsilyl)amide, lithiumbis(trimethylsilyl)amide, etc., preferably aliphatic tertiary amines,aliphatic cyclic tertiary amines or pyridines, more preferablytriethylamine, 1,4-diazabicyclo[2.2.2]octane (DABCO), pyridine or4-(N,N-dimethylamino)pyridine.

An amount of the base to be used in the reaction is generally 0.5 to 20mols, preferably 1 to 5 mols based on 1 mol of Compound (Ib).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be ketones such as acetone,methyl isobutyl ketone, etc.; nitrites such as acetonitrile, etc.;esters such as ethyl acetate, etc.; halogenated hydrocarbons such asmethylene chloride, chloroform, dichloroethane, etc.; ethers such asdiethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbonssuch as toluene, etc.; aliphatic hydrocarbons such as hexane,cyclohexane, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; or a mixed solvent ofthe above, preferably nitriles, halogenated hdyrocarbons or ethers, morepreferably acetonitrile or methylene chloride.

The reaction temperature may vary mainly depending on startingmaterials, reaction reagents and a kind of the solvent to be used, andusually −90° C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 48 hours, preferably 15 minutes to 12hours.

Incidentally, in the present step, a conventionally known method can beemployed as usual protection of a hydroxyl group.

In the above formula, R², R³, R⁴, R⁵, R⁶, R⁷, X and Y have the samemeanings as defined above, R^(1a) represents the same meaning as R¹except for removing a hydrogen atom.

Step J is a step to produce Compound (Ii) of the present invention or acompound represented by the formula (XVIII), in which a hydroxyl groupis protected, by reducing, oxidizing and then metalating a6-chloropyridazine derivative represented by the formula (IVa), andreacting the resulting material with an electrophilic agent to introducea substituent on the 6-position of a pyridazine ring, and furthersubjecting to chlorination, and substitution reaction with an oxygennucleophilic agent, and further, a step to produce Compound (Ij) of thepresent invention by removing the protective group of Compound (XVIII).

(Step J-1)

Step J-1 is a step to produce Compound (IVb) in which R¹ in Compound(IV) is a hydrogen atom by reacting Compound (IVa) in which R¹ inCompound (IV) is a chlorine atom with a reducing agent in the presenceor absence of a solvent.

The reducing agent to be used in the reaction is not specificallylimited so long as it can reduce a chlorine atom on an aromatic ring,and for example, it may be a reducing agent to be used in a usualhydrogenation reaction, preferably hydrogen-palladium catalyst.

When the hydrogenation reaction is carried out in the present step, ahydrogen pressure is generally 1 atm to 100 atms, preferably 1 to 3atms.

An amount of the palladium to be used in the hydrogenation reaction isgenerally 0.001 to 10 mols, preferably 0.01 to 1 mol based on 1 mol ofCompound (IVa).

The hydrogenation reaction is preferably carried out in the presence ofa base.

The base to be used is not specifically limited so long as it is a baseshowing a pH of generally 8 or more, and for example, alkali metalhydroxides such as sodium hydroxide, potassium hydroxide, etc.; alkalimetal carbonates such as sodium carbonate, potassium carbonate, cesiumcarbonate, etc.; metal alkoxides such as sodium methoxide, sodiumethoxide, potassium t-butoxide, etc.; alkali metal hydrides such assodium hydride, potassium hydride, etc.; aqueous ammonia; aliphatictertiary amines such as triethylamine, tri-n-butylamine,diisopropylethylamine, etc.; aliphatic cyclic tertiary amines such as1,4-diazabicyclo[2.2.2]octane (DABCO),1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU), etc.; pyridines such aspyridine, collidine, 4-(N,N-dimethylamino)pyridine, etc.; ororganometallic bases such as butyl lithium, s-butyl lithium, lithiumdiisopropylamide, sodium bis(trimethylsilyl)amide, lithiumbis(trimethylsilyl)amide, etc., preferably aqueous ammonia or aliphatictertiary amines, more preferably aqueous ammonia or triethylamine.

An amount of the base to be used in the reaction is generally 0.1 to 100mols, preferably 1 to 3 mols based on 1 mol of Compound (IVa).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be water; alcohols such asmethanol, ethanol, t-butanol, etc.; ketones such as acetone, methylisobutyl ketone, etc.; nitriles such as acetonitrile, etc.; esters suchas ethyl acetate, etc.; halogenated hydrocarbons such as methylenechloride, chloroform, dichloroethane, etc.; ethers such as diethylether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such astoluene, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; aliphatic hydrocarbonssuch as hexane, cyclohexane, etc.; or a mixed solvent of the above,preferably alcohols, more preferably methanol or ethanol.

The reaction temperature may vary mainly depending on startingmaterials, reaction reagents and a kind of the solvent to be used, andusually −90° C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 48 hours, preferably 15 minutes to 12hours.

(Step J-2)

Step J-2 is a step to produce Pyridazine N-oxide represented by theformula (XV) by oxidizing Compound (IVb) with an oxidizing agent in thepresence or absence of a solvent.

The present step can be carried out in accordance with Step B-1 or C-1.

(Step J-3)

Step J-3 is a step to produce Compound (XVI) of the present invention byreacting Compound (XV) with a metalating agent in the presence orabsence of a solvent, and then, reacting with an electrophilic agent.

The present step can be carried out in accordance with Step G-1.

(Step J-4)

Step J-4 is a step to produce Compound (XVII) by reacting Compound (XVI)with phosphorus oxychloride in the presence or absence of a solvent.

The present step is similar to Step B-3 or C-2.

(Step J-5)

Step J-5 is a step to produce Compound (Ii) of the present invention ora compound represented by the formula (XVIII), in which a hydroxyl groupis protected, by reacting Compound (XVII) with an oxygen nucleophilicagent represented by the formula (VI) in the presence or absence of asolvent, and if necessary, in the presence of a base.

The present step is similar to Step A-3, B-4 or C-3.

(Step J-6)

Step J-6 is a step to produce Compound (Ij) of the present invention byremoving the protective group for a hydroxyl group of Compound (XVIII).

The present step is similar to Step A-4, B-5, C-4, D-2, E-3, F-2 or G-2.

In the above formula, R^(1a), R², R³, R⁴, R⁵, R⁶, R⁷, X and Y have thesame meanings as defined above.

Step K is a step to produce Compound (Ii) of the present invention or acompound represented by the formula (XVIII), in which a hydroxyl groupis protected, by oxidizing, dechlorinating and then metalating6-chloropyridazine derivative represented by the formula (Ik) of thepresent invention or a 6-chloropyridazine derivative represented by theformula (XIX) in which a hydroxyl group is protected, then introducingan electrophilic agent and finally reducing the resulting material, andfurther a step to produce Compound (Ij) of the present invention byremoving the protective group of Compound (XVIII).

(Step K-1)

Step K-1 is a step to produce a N-oxypyridazine compound represented bythe formula (Il) or (XX) by oxidizing Compound (Ik) or Compound (XIX)with an oxidizing agent in the presence or absence of a solvent.

The present step can be carried out in accordance with Step B-1, C-1 orJ-2.

(Step K-2)

Step K-2 is a step to produce a N-oxide compound (Im) or (XXI), in whichthe 6-position of the pyridazine ring is a hydrogen atom, by reacting aN-oxide compound (Il) or (XX), in which the 6-position of the pyridazinering is a chlorine atom, with a reducing agent in the presence orabsence of a solvent.

The present step can be carried out in accordance with Step J-1.

(Step K-3)

Step K-3 is a step to produce Compound (In) of the present invention ora compound represented by the formula (XXII), in which a hydroxyl groupis protected, by reacting Compound (Im) or (XXI) with a metalating agentin the presence or absence of a solvent, and then, reacting with anelectrophilic agent.

The present step can be carried out in accordance with Step G-1 or J-3.

(Step K-4)

Step K-4 is a step to produce Compound (Ii) of the present invention ora compound represented by the formula (XVIII), in which a hydroxyl groupis protected, by reacting a N-oxide derivative represented by theformula (In) or (XXII) with phosphorus trichloride or phosphorustribromide in the presence or absence of a solvent.

An amount of the phosphorus trichloride or phosphorus tribromide to beused is generally 0.5 to 100 mols, preferably 1 to 20 mols based on 1mol of Compound (In) or (XXII).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be halogenated hydrocarbons suchas methylene chloride, chloroform, dichloroethane, etc.; ethers such asdiethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbonssuch as toluene, etc.; amides such as dimethylformamide,dimethylacetamide, etc.; sulfoxides such as dimethylsulfoxide, etc.;aliphatic hydrocarbons such as hexane, cyclohexane, heptane, etc.; or amixed solvent of the above, preferably halogenated hydrocarbons, morepreferably chloroform.

The reaction temperature may vary mainly depending on startingmaterials, reaction reagents and a kind of the solvent to be used, andusually −90° C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 24 hours, preferably 15 minutes to 6hours.

(Step K-5)

Step K-5 is a step to produce Compound (Ij) of the present invention byremoving the protective group for a hydroxyl group of Compound (XVIII).

The present step is similar to Step A-4, B-5, C-4, D-2, E-3, F-2, G-2 orJ-6.

In the above formula, R², R³, R⁴, R⁵, R⁶, R⁷, X and Y have the samemeanings as defined above, R^(1b) represents the same meaning as R¹except for removing a hydrogen atom and a halogen atom.

Step L is a step to produce Compound (Io) or a compound represented bythe formula (XXIII), in which a hydroxyl group is protected, by reactinga 6-chloropyridazine derivative represented by the formula (Ik) or (XIX)with an organometallic compound, and further a step to produce Compound(Ip) of the present invention by removing the protective group ofCompound (XXIII).

(Step L-1)

Step L-1 is a step to produce Compound (Io) of the present invention ora compound represented by the formula (XXIII), in which a hydroxyl groupis protected, by reacting Compound (Ik) or (XIX) with an organometalliccompound in the presence or absence of a solvent and in the presence ofa metal catalyst.

The organometallic compound to be used is not specifically limited solong as it is used for a cross-coupling reaction in which a R^(1b) groupis substituted by a chlorine atom, and for example, it may be organicmagnesium compounds such as methyl magnesium chloride, ethyl magnesiumbromide, phenylmagnesium chloride, etc.; organic zinc compounds such asphenyl zinc chloride, etc.; organic aluminum compounds such as(diisobutyl)(1-hexenyl)aluminum, etc.; organic tin compounds such as(vinyl)trimethyl tin, (1-ethoxyvinyl)tributyltin, (2-furyl)tributyltin,(2-thienyl)tributyltin, etc.; organic boron compounds such asphenylboronic acid, etc.; organic silicate compounds such astrimethylvinylsilicon-tris(dimethylamino)sulfonium difluorotrimethylsilicate, etc.; potassium cyanide, and acetylene compounds such astrimethylsilyl acetylene, phenyl acetylene, etc. may be used similarlyin the presence of amines such as triethylamine, etc., as in theabove-mentioned organometallic compounds, preferably organic tincompounds or organic boron compounds.

An amount of the organometallic compound to be used in the reaction isgenerally 0.5 to 10 mols, preferably 1 to 2 mols based on 1 mol ofCompound (Ik) or (XIX).

The metal catalyst to be used in the present step is not specificallylimited so long as it can be used in a cross-coupling reaction, and forexample, it may be a nickel catalyst or a palladium catalyst.

An amount of the metal catalyst to be used in the reaction is generally0.0001 to 10 mols, preferably 0.01 to 0.5 mol based on 1 mol of Compound(Ik) or (XIX).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be water; alcohols such asmethanol, ethanol, t-butanol, etc.; ketones such as acetone, methylisobutyl ketone, etc.; nitrites such as acetonitrile, etc.; esters suchas ethyl acetate, etc.; halogenated hydrocarbons such as methylenechloride, chloroform, dichloroethane, etc.; ethers such as diethylether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such astoluene, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; aliphatic hydrocarbonssuch as hexane, cyclohexane, etc.; organic amines such as triethylamine,pyridine, etc.; or a mixed solvent of the above, preferably ethers,aromatic hydrocarbons or amides, more preferably ether, tetrahydrofuran,toluene or dimethylformamide.

The reaction temperature may vary mainly depending on startingmaterials, reaction reagents and a kind of the solvent to be used, andusually −90° C. to 200° C., preferably 0° C. to 130° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 48 hours, preferably 15 minutes to 24hours.

(Step L-2)

Step L-2 is a step to produce Compound (Ip) of the present invention byremoving the protective group for a hydroxyl group of Compound (XXIII).

The present step is similar to Step A-4, B-5, C-4, D-2, E-3, F-2, G-2,J-6 or K-5.

In the above formula, R², R³, R⁴, R⁵, R⁶, R⁷, X and Y have the samemeanings as defined above.

Step M is a step to produce Compound (Iq) of the present invention or acompound represented by the formula (XXIV), in which a hydroxyl group isprotected, by cyanation of 6-position unsubstituted Pyridazine N-oxidederivative represented by the formula (Im) or (XXI), and also a step toproduce Compound (Ir) of the present invention by removing theprotective group of Compound (XXIV).

(Step M-1)

Step M-1 is a step to produce Compound (Iq) of the present invention ora compound represented by the formula (XXIV), in which a hydroxyl groupis protected, by reacting Compound (Im) or (XXI) with a cyanationreagent in the presence or absence of a solvent.

The present step can be carried out in accordance with theconventionally known Reissert-Henze reaction (JOC, 48, 1983, 1375 to1377; Heterocycles, 15, 1981, 981 to 984; Synthesis, 1983, 316 to 319,etc.).

(Step M-2)

Step M-2 is a step to produce Compound (Ir) of the present invention byremoving the protective group for a hydroxyl group of Compound (XXIV).

The present step is similar to Step A-4, B-5, C-4, D-2, E-3, F-2, G-2,J-6, K-5 or L-2.

In the above formula, R², R³, R⁴, R⁵, R⁶, R⁷, X and Y have the samemeanings as defined above.

Step N is a step to produce Compound (Is) of the present invention or acompound represented by the formula (XXV), in which a hydroxyl group isprotected, by dechlorinating a 6-chloropyridazine derivative representedby the formula (Ik) or (XIX), and further a step to produce Compound(It) of the present invention by removing the protective group ofCompound (XXV).

(Step N-1)

Step N-1 is a step to produce Compound (Is) of the present invention ora compound represented by the formula (XXV), in which a hydroxyl groupis protected, by reacting Compound (Ik) or (XIX) with a reducing agentin the presence or absence of a solvent.

The present step can be carried out in accordance with Step J-1 or K-2.

(Step N-2)

Step N-2 is a step to produce Compound (It) of the present invention byremoving the protective group for a hydroxyl group of Compound (XXV).

The present step is similar to Step A-4, B-5, C-4, D-2, E-3, F-2, G-2,J-6, K-5, L-2 or M-2.

In the above formula, R¹, R², R⁴, R⁵, R⁶ and R⁷ have the same meaningsas defined above.

Step O is a step to produce Compound (Iu) of the present invention byreacting a 3,4-dichloropyridazine derivative represented by the formula(XXVI) with a catechol derivative represented by the formula (XXVII) andthen subjecting the resulting material to hydrolysis.

(Step O-1)

Step O-1 is a step to produce a condensed compound represented by theformula (XXVIII) by reacting Compound (XXVI) with Compound (XXVII) inthe presence or absence of a solvent, and if necessary, in the presenceof a base.

The present step can be carried out in accordance with Step A-1, B-2,D-1 or E-2, and an amount of the base to be used is generally 1 to 10mols, preferably 2 to 6 mols based on 1 mol of Compound (XXVI).

(Step O-2)

Step O-2 is a step to produce Compound (Iu) of the present invention bysubjecting Compound (XXVIII) to hydrolysis.

The present step can be carried out in accordance with the case where Yis a hydrogen atom in Step A-3, B-4 or C-3, and a reaction temperatureis preferably 80° C. to 100° C.

In the above formula, R², R³, R⁴, R⁵, R⁶ and R⁷ have the same meaningsas defined above.

Step P is a step to produce Compound (Iv) of the present invention or acompound represented by the formula (XXXI), in which a hydroxyl group isprotected, by selectively subjecting 6-position of a4,6-dichloropyridazine derivative represented by the formula (Va) tohydrolysis to prepare Compound (XXIX), then, brominating 4,6-positionsthereof with phosphorus oxybromide, and then selectively reacting anoxygen nucleophilic agent at 4-position thereof, and a step to produceCompound (Iw) of the present invention by removing the protective groupof Compound (XXXI).

(Step P-1)

Step P-1 is a step to produce a compound represented by the formula(XXIX) by subjecting Compound (Va) to hydrolysis in the presence orabsence of a solvent and in the presence of an acid to selectivelyconvert a chlorine atom at the 6-position into a hydroxyl group.

An acid to be used is not specifically limited so long as it is an acidshowing a pH of 6 or less, and for example, it may be organic acids suchas formic acid, acetic acid, oxalic acid, propionic acid, succinic acid,maleic acid, fumalic acid, benzoic acid, etc.; mineral acids such ashydrofluoric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid,sulfuric acid, nitric acid, phosphoric acid, etc.; or Lewis acids suchas aluminum chloride, iron chloride, titanium chloride, borontrifluoride, etc., preferably organic acids, more preferably formic acidor acetic acid.

The present step is carried out preferably in the presence of a metalsalt of an acid.

The metal salt of an acid to be used may inclide, for example, alkalimetal salts of an organic acid such as sodium formate, potassiumformate, lithium acetate, sodium acetate, potassium acetate, cesiumacetate, sodium benzoate, etc.; alkaline earth metal salts of an organicacid such as magnesium formate, calcium formate, magnesium acetate,calcium acetate, magnesium benzoate, etc.; alkali metal salts oralkaline earth metal salts of carbonic acid such as sodium carbonate,potassium carbonate, calcium carbonate, sodium hydrogen carbonate,potassium hydrogen carbonate, etc.; or alkali metal salts or alkalineearth metal salts of a mineral acid such as sodium fluoride, potassiumfluoride, sodium chloride, potassium chloride, sodium bromide, potassiumbromide, sodium iodide, potassium iodide, sodium sulfate, sodiumhydrogen sulfate, potassium sulfate, potassium hydrogen sulfate,magnesium sulfate, sodium phosphate, disodium hydrogen phosphate, sodiumdihydrogen phosphate, potassium phosphate, dipotassium hydrogenphosphate, potassium dihydrogen phosphate, etc., preferably alkali metalsalts of an organic acid, more preferably sodium formate, potassiumformate, sodium acetate or potassium acetate.

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be water; alcohols such asmethanol, ethanol, t-butanol, etc.; ketones such as acetone, methylisobutyl ketone, etc.; nitriles such as acetonitrile, etc.; esters suchas ethyl acetate, etc.; halogenated hydrocarbons such as methylenechloride, chloroform, dichloroethane, etc.; ethers such as diethylether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbons such astoluene, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; organic acids such asformic acid, acetic acid, propionic acid, etc.; or a mixed solvent ofthe above, preferably water, nitriles, ethers, amides, sulfoxides ororganic acids, more preferably water, acetonitrile, tetrahydrofuran,dioxane, dimethylformamide, dimethylsulfoxide, formic acid or aceticacid.

The reaction temperature may vary depending on the starting compounds,reaction reagents and a kind of the solvent to be used, etc., and isgenerally −90° C. to 200° C., preferably 0° C. to 150° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually, 5 minutes to 24 hours, preferably 15 minutes to 12hours.

(Step P-2)

Step P-2 is a step to produce Compound (XXX) by reacting Compound (XXIX)with phosphorus oxybromide in the presence or absence of a solvent.

An amount of the phosphorus oxybromide to be used in the present step isgenerally 0.5 to 100 mols, preferably 1 to 10 mols based on 1 mol ofCompound (XXIX).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be ketones such as acetone,methyl isobutyl ketone, etc.; nitriles such as acetonitrile, etc.;esters such as ethyl acetate, etc.; halogenated hydrocarbons such asmethylene chloride, chloroform, dichloroethane, etc.; ethers such asdiethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbonssuch as toluene, etc.; amides such as dimethylformamide,dimethylacetamide, etc.; sulfoxides such as dimethylsulfoxide, etc.;aliphatic hydrocarbons such as hexane, cyclohexane, etc.; or a mixedsolvent of the above, preferably halogenated hydrocarbons, morepreferably methylene chloride, chloroform.

The reaction temperature may vary depending on starting materials,reaction reagents and a kind of the solvent to be used, and usually −90°C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 72 hours, preferably 30 minutes to 24hours.

(Step P-3)

Step P-3 is a step to produce Compound (Iv) of the present invention ora compound represented by the formula (XXXI), in which a hydroxyl groupis protected, by reacting Compound (XXX) with an oxygen nucleophilicagent represented by the formula (VI) in the presence or absence of asolvent, and if necessary, in the presence of a base.

The present step is similar to Step A-3, B-4, C-3 or J-5.

(Step P-4)

Step P-4 is a step to produce Compound (Iw) of the present invention byremoving the protective group for a hydroxyl group of Compound (XXXI).

The present step is similar to Step A-4, B-5, C-4, D-2, E-3, F-2, G-2,J-6, K-5, L-2, M-2 or N-2.

In the above formula, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the samemeanings as defined above, a compound represented by the formula (XXXII)represents an oxygen nucleophilic agent, a sulfur nucleophilic agent ora nitrogen nucleophilic agent, Z represents a substituent in which aproton is removed from the oxygen nucleophilic agent, the sulfurnucleophilic agent or the nitrogen nucleophilic agent, and for example,it may be an alkoxy group, a thioalkoxy group, a dialkylamino group,etc.

Step Q is a step to convert a hydroxy isomer represented by the formula(Ib) of the present invention into an ester derivative represented bythe formula (Iy) of the present invention.

(Step Q-1)

Step Q-1 is a step to produce Compound (Ix) of the present invention byreacting Compound (Ib) of the present invention with phosgene in thepresence or absence of a solvent.

An amount of the phosgene to be used in the reaction is generally 0.5 to10 mols, preferably 1 to 3 mols based on 1 mol of Compound (Ib).

The reaction is preferably carried out in the presence of a base.

The base to be used is not specifically limited so long as it is a basegenerally showing a pH of 8 or more, and for example, alkali metalhydroxides such as sodium hydroxide, potassium hydroxide, etc.; alkalimetal carbonates such as sodium carbonate, potassium carbonate, cesiumcarbonate, etc.; metal alkoxides such as sodium methoxide, sodiumethoxide, potassium t-butoxide, etc.; alkali metal hydrides such assodium hydride, potassium hydride, etc.; aliphatic tertiary amines suchas triethylamine, tributylamine, diisopropylethylamine, etc.; aliphaticcyclic tertiary amines such as 1,4-diazabicyclo-[2.2.2]octane (DABCO),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), etc.; pyridines such aspyridine, collidine, 4-(N,N-dimethylamino)pyridine, etc.; or, organicmetal bases such as n-butyl lithiums, s-butyl lithium, lithiumdiisopropylamide, sodium bis(trimehylsilyl)amide, lithiumbis(trimethylsilyl)amide, etc., preferably aliphatic tertiary amines,aliphatic cyclic tertiary amines or pyridines, more preferablytriethylamine, 1,4-diazabicyclo[2.2.2]octane (DABCO), pyridine or4-(N,N-dimethylamino)pyridine.

An amount of the base to be used in the reaction is generally 0.5 to 20mols, preferably 1 to 5 mols based on 1 mol of Compound (Ib).

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be ketones such as acetone,methyl isobutyl ketone, etc.; nitriles such as acetonitrile, etc.;esters such as ethyl acetate, etc.; halogenated hydrocarbons such asmethylene chloride, chloroform, dichloroethane, etc.; ethers such asdiethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbonssuch as toluene, etc.; aliphatic hydrocarbons such as hexane,cyclohexane, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; or a mixed solvent ofthe above, preferably nitriles, halogenated hydrocarbons or ethers, morepreferably acetonitrile or methylene chloride.

The reaction temperature may vary mainly depending on startingmaterials, reaction reagents and a kind of the solvent to be used, andusually −90° C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 48 hours, preferably 15 minutes to 12hours.

(Step Q-2)

Step Q-2 is a step to produce Compound (Iy) of the present invention byreacting Compound (Ix) of the present invention with a nucleophilicagent represented by the formula (XXXII) in the presence or absence of asolvent, and if necessary, in the presence of a base.

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, and for example, it may be ketones such as acetone,methyl isobutyl ketone, etc.; nitriles such as acetonitrile, etc.;esters such as ethyl acetate, etc.; halogenated hydrocarbons such asmethylene chloride, chloroform, dichloroethane, etc.; ethers such asdiethyl ether, tetrahydrofuran, dioxane, etc.; aromatic hydrocarbonssuch as toluene, etc.; aliphatic hydrocarbons such as hexane,cyclohexane, etc.; amides such as dimethylformamide, dimethylacetamide,etc.; sulfoxides such as dimethylsulfoxide, etc.; or a mixed solvent ofthe above, preferably nitriles, halogenated hydrocarbons or ethers, morepreferably acetonitrile or methylene chloride.

The base to be used is not specifically limited so long as it is a basegenerally showing a pH of 8 or more, and for example, alkali metalhydroxides such as sodium hydroxide, potassium hydroxide, etc.; alkalimetal carbonates such as sodium carbonate, potassium carbonate, cesiumcarbonate, etc.; metal alkoxides such as sodium methoxide, sodiumethoxide, potassium t-butoxide, etc.; alkali metal hydrides such assodium hydride, potassium hydride, etc.; aliphatic tertiary amines suchas triethylamine, tributylamine, diisopropylethylamine, etc.; aliphaticcyclic tertiary amines such as 1,4-diazabicyclo-[2.2.2]octane (DABCO),1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), etc.; pyridines such aspyridine, collidine, 4-(N,N-dimethylamino)pyridine, etc.; or organicmetal bases such as n-butyl lithiums, s-butyl lithium, lithiumdiisopropylamide, sodium bis(trimehylsilyl)amide, lithiumbis(trimethylsilyl)amide, etc., preferably aliphatic tertiary amines,aliphatic cyclic tertiary amines or pyridines, more preferablytriethylamine, 1,4-diazabicyclo[2.2.2]octane (DABCO), pyridine or4-(N,N-dimethylamino)pyridine.

An amount of the base to be used in the reaction is generally 0.5 to 20mols, preferably 1 to 5 mols based on 1 mol of Compound (Ix).

The nucleophilic agent (XXXII) to be used in the reaction is notspecifically limited so long as it can substitute a chlorine atom ofchlorocarbonic acid ester (Ix), and the oxygen nucleophilic agent mayinclude, for example, alcohols such as methanol, ethanol, propanol,etc.; or phenols such as phenol, 4-chlorophenol, etc., also, the sulfurnucleophilic agent may include, for example, thiols such asmethanethiol, ethanethiol, propanethiol, etc.; or thiophenols such asthiophenol, etc., and, the nitrogen nucleophilic agent may include, forexample, aliphatic linear amines such as methylamine, dimethylamine,diethylamine, methyl(t-butyl)amine, methyl(cyanomethyl)amine,methyl(ethoxycarbonylmethyl)amine, bis(cyanomethyl)amine,bis(2-cyanoethyl)amine, bis(ethoxycarbonylmethyl)amine,bis(2-methoxyethyl)amine, bis(2-ethoxyethyl)amine,bis(2-chloroethyl)amine, N,O-dimethylhydroxylamine, etc.; aromaticamines such as methyl(phenyl)amine, methyl(pyridyl)amine, etc.;aliphatic cyclic amines such as aziridine, azetidine, pyrrolidine,piperidine, morpholine, thiomorpholine, N-methylpiperazine,N-phenylpiperazine, 2-methoxycarbonylpyrrolidine, 3-hydroxypyrrolidine,4-bromopiperidine, 4-methylpiperidine, 2,2,6,6-tetramethylpiperidine,2-ethoxycarbonylpiperidine, 4-ethoxycarbonylpiperidine, 2,6-dimethylmorpholine, 1,2,3,4-tetrahydroisoquinoline, etc.; aromatic cyclic aminessuch as carbazole, 2,5-dimethylpyrrole, etc., preferably methanol,ethanol, methanethiol, ethanethiol, methylamine, dimethylamine,methyl(cyanomethyl)amine, methyl(ethoxycarbonylmethyl)amine,bis(cyanomethyl)amine, bis(2-cyanoethyl)amine,bis(ethoxycarbonylmethyl)amine, bis(2-methoxyethyl)amine,bis(2-ethoxyethyl)amine, bis(2-chloroethyl)amine,N,O-dimethylhydroxylamine, methyl(pyridyl)amine, azetidine, pyrrolidine,piperidine, morpholine, thio morpholine, N-methylpiperazine,2-methoxycarbonylpyrrolidine, 3-hydroxypyrrolidine,2-ethoxycarbonylpiperidine, 4-ethoxycarbonylpiperidine, 2,6-dimethylmorpholine, 2,5-dimethylpyrrole, more preferably dimethylamine,methyl(cyanomethyl)amine, methyl(ethoxycarbonylmethyl)amine,bis(cyanomethyl)amine, bis(ethoxycarbonylmethyl)amine,bis(2-methoxyethyl)amine, bis(2-ethoxyethyl)amine,N,O-dimethylhydroxylamine, azetidine, morpholine, thiomorpholine,N-methylpiperazine, 2-methoxycarbonylpyrrolidine, 3-hydroxypyrrolidine,2-ethoxycarbonylpiperidine, 4-ethoxycarbonylpiperidine, 2,6-dimethylmorpholine.

An amount of the nucleophilic agent to be used in the reaction isgenerally 0.5 to 20 mols, preferably 1 to 5 mols based on 1 mol ofCompound (Ix).

The reaction temperature may vary mainly depending on startingmaterials, reaction reagents and a kind of the solvent to be used, andusually −90° C. to 200° C., preferably 0° C. to 100° C.

The reaction time may vary mainly depending on a reaction temperature,starting materials, reaction reagents and a kind of the solvent to beused, and usually 5 minutes to 48 hours, preferably 15 minutes to 12hours.

Incidentally, after completion of the above-mentioned respective steps,and before the steps subsequent thereto, the functional group(s) in R¹to R⁷ of the desired compound of the respective steps can be convertedto the other functional group so long as it is within the definitionsfor R¹ to R⁷.

Also, in Steps A-1, B-2, D-1 and E-2, when at least one of R¹ and R² isa chlorine atom, depending on the reaction conditions, in the Step, achlorine atom of R¹ or R² is substituted by the group

in some cases, and further, in Steps A-3, B-4, C-3 and J-5, when atleast either one of R¹ and R² is a chlorine atom, depending on thereaction conditions, in the Step, a chlorine atom of R¹ or R² issubstituted by the group OY in some cases, and further, in Step P-3, abromine atom at the 6-position of the pyridazine ring or a chlorine atomof R² when R² is a chlorine atom is substituted by the group OY in somecases.

Starting Compound (II) in Step A and B may be used those commerciallyavailable, or may be produced by the method disclosed in, for example,Kogyo Kagaku Zasshi (Journal of Industrial Chemistry), 1971, vol. 74,No. 7, pp. 1490-1491; Tetrahedron, 1999, vol. 55, No. 52, pp. 15067 to15070; The Journal of Organic Chemistry, 1963, vol. 28, pp. 218 to 221or in accordance with these methods.

The starting Compound (X) of Steps D and E can be produced by the methoddisclosed in, for example, Helvetica Chimica Acta, 1956, vol. 39, pp.1755 to 1764; Monatshefte fur Chemie, 1968, vol. 99, pp. 15-81 (in thepresent specification, the letter u in Monatshefte fur Chemie representsu-umlaut.); German Patent 1,912,472, Nov. 12, 1970 (filed on Apr. 12,1969) (Ger. Offen. 1,912,472, 12 Nov. 1970, Appl. 12 Mar. 1969), or inaccordance with these methods.

The phenol Compound (III) to be used in Steps A, B, D and E may be usedthose commercially available, or may be produced by using theconventionally known method or in accordance with these methods.

2-Isobutylphenol can be produced by the method disclosed in, forexample, Canadian Journal of Chemistry, 1956, vol. 34, pp. 851-854.

2-Pentylphenol can be produced by the method disclosed in, for example,Tetrahedron Letters, 1989, vol. 30, No. 35, pp. 4741-4744.

2-Hexylphenol can be produced by the method disclosed in, for example,Journal of the Chemical Society: Parkin transaction I, 2000, vol. 7, pp.1109-1116 (coversion of vinyl group into hexyl group), and Journal ofMedicinal Chemistry, 1977, vol. 20, No. 10, pp. 1317-1323 (conversion ofphenylmethyl ether into phenol, demethylation reaction) fromcommercially available 1-methoxy-2-vinylbenzene.

2-Cyclopropylphenol can be produced by the method disclosed in, forexample, Bioorganic & Medicinal Chemistry, 1997, vol. 5, No. 10, pp.1959-1968.

2-(1-Methylcyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, from commercially available1-(2-methoxyphenyl)ethanone, The Journal of Organic Chemistry, 1963,vol. 28, p. 1128 or Synthetic Communications, 1985, vol. 15, No. 10, pp.855-864 (conversion of carbonyl group into olefin, Wittg reaction), andby the method disclosed in Organic Reactions, 1973, vol. 20, pp. 1-131or Journal of the American Chemical Society, 1975, vol. 97, p. 3428 orTetrahedron Letters, 1998, vol. 39, pp. 8621-8624 (construction ofcyclopropyl group, Simmons-Smith reaction), and by the method disclosedin Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9,pp. 1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-(1-Ethylcyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, from commercially available1-(2-methoxyphenyl)-1-propanone, The Journal of Organic Chemistry, 1963,vol. 28, p. 1128 or Synthetic Communications, 1985, vol. 15, No. 10, pp.855-864 (conversion of carbonyl group into olefin, Wittg reaction), andby the method disclosed in Organic Reactions, 1973, vol. 20, pp. 1-131or Journal of the American Chemical Society, 1975, vol. 97, p. 3428 orTetrahedron Letters, 1998, vol. 39, pp. 8621-8624 (construction ofcyclopropyl group, Simmons-Smith reaction), and by the method disclosedin Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9,pp. 1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-(1-Cyclopropylcyclopropyl)phenol can be produced in accordance withthe method disclosed in, for example, Organic Synthesis, CollectiveVolume, vol. 4, pp. 836-838 (conversion of phenol into phenyl methylether, methylation reaction), and the method disclosed in The Journal ofOrganic Chemistry, 1963, vol. 28, p. 1128 or Synthetic Communications,1985, vol. 15, No. 10, pp. 855-864 (conversion of carbonyl group intoolefin, Wittg reaction), and the method disclosed in Organic Reactions,1973, vol. 20, pp. 1-131 or Journal of the American Chemical Society,1975, vol. 97, p. 3428 or Tetrahedron Letters, 1998, vol. 39, pp.8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction),and by the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction) fromcyclopropyl(2-hydroxyphenyl)methanone produced by the method disclosedin Journal of the Chemical Society: Parkin transaction I, 1990, pp.689-693 from commercially available 2,3-dihydro-4H-chromen-4-one.

1-(2-Hydroxyphenyl)cyclopropanecarbonitrile can be produced by producing1-(2-methoxyphenyl)cyclopropanecarbonitrile in accordance with themethod disclosed in, for example, Journal of the American ChemicalSociety, 2000, vol. 122, No. 4, pp. 712-713, and by the method disclosedin Organic Synthesis, Collective Volume, vol. 5, pp. 412-414 (conversionof phenylmethyl ether into phenol, demethylation reaction).

2-(1-Phenylcyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, from commercially available1-(2-methoxyphenyl)(phenyl)methanone, The Journal of Organic Chemistry,1963, vol. 28, p. 1128 or Synthetic Communications, 1985, vol. 15, No.10, pp. 855-864 (conversion of carbonyl group into olefin, Wittgreaction), and by the method disclosed in Organic Reactions, 1973, vol.20, pp. 1-131 or Journal of the American Chemical Society, 1975, vol.97, p. 3428 or Tetrahedron Letters, 1998, vol. 39, pp. 8621-8624(construction of cyclopropyl group, Simmons-Smith reaction), and by themethod disclosed in Bioscience, Biotechnology, and Biochemistry, 1993,vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional Patent PublicationNo. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

2-(2-Methylcyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, from commercially available1-(chloromethyl)-2-methoxybenzene, Journal of the American ChemicalSociety, 1973, vol. 95, No. 2, pp. 581-582 (construction of cyclopropylgroup), and by the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

2-(2,2-Dimethylcyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, from commercially available1-(chloromethyl)-2-methoxybenzene, Journal of the American ChemicalSociety, 1973, vol. 95, No. 2, pp. 581-582 (construction of cyclopropylgroup), and by the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

2-[(Cis-2,cis-3-dimethyl)-ref-1-cyclopropyl]phenol can be produced inaccordance with the method disclosed in, for example, from commerciallyavailable 1-(chloromethyl)-2-methoxybenzene, Journal of the AmericanChemical Society, 1973, vol. 95, No. 2, pp. 581-582 (construction ofcyclopropyl group), and by the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-[(Cis-2,trans-3-dimethyl)-ref-1-cyclopropyl]phenol can be produced inaccordance with the method disclosed in, for example, from commerciallyavailable 1-(chloromethyl)-2-methoxybenzene, Journal of the AmericanChemical Society, 1973, vol. 95, No. 2, pp. 581-582 (construction ofcyclopropyl group), and by the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-[(Trans-2,trans-3-dimethyl)-ref-1-cyclopropyl]phenol can be producedin accordance with the method disclosed in, for example, fromcommercially available 1-(chloromethyl)-2-methoxybenzene, Journal of theAmerican Chemical Society, 1973, vol. 95, No. 2, pp. 581-582(construction of cyclopropyl group), and by the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-[(Ref-1,cis-5,cis-6)-bicyclo[3.1.0]hexa-6-yl]phenol can be produced inaccordance with the method disclosed in, for example, from commerciallyavailable 1-(chloromethyl)-2-methoxybenzene, Journal of the AmericanChemical Society, 1973, vol. 95, No. 2, pp. 581-582 (construction ofcyclopropyl group), and by the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-[(Ref-1,cis-5,trans-6)-bicyclo[3.1.0]hexa-6-yl]phenol can be producedin accordance with the method disclosed in, for example, fromcommercially available 1-(chloromethyl)-2-methoxybenzene, Journal of theAmerican Chemical Society, 1973, vol. 95, No. 2, pp. 581-582(construction of cyclopropyl group), and by the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-[(Ref-1,cis-6,cis-7)-bicyclo[4.1.0]hept-7-yl]phenol can be produced inaccordance with the method disclosed in, for example, from commerciallyavailable 1-(chloromethyl)-2-methoxybenzene, Journal of the AmericanChemical Society, 1973, vol. 95, No. 2, pp. 581-582 (construction ofcyclopropyl group), and by the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-[(Ref-1,cis-6,trans-7)-bicyclo[4.1.0]hept-7-yl]phenol can be producedin accordance with the method disclosed in, for example, fromcommercially available 1-(chloromethyl)-2-methoxybenzene, Journal of theAmerican Chemical Society, 1973, vol. 95, No. 2, pp. 581-582(construction of cyclopropyl group), and by the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-[(2,2,Cis-3-trimethyl)-ref-1-cyclopropyl]phenol can be produced inaccordance with the method disclosed in, for example, from commerciallyavailable 1-(chloromethyl)-2-methoxybenzene, Journal of the AmericanChemical Society, 1973, vol. 95, No. 2, pp. 581-582 (construction ofcyclopropyl group), and by the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-[(2,2,trans-3-trimethyl)-ref-1-cyclopropyl]phenol can be produced inaccordance with the method disclosed in, for example, from commerciallyavailable 1-(chloromethyl)-2-methoxybenzene, Journal of the AmericanChemical Society, 1973, vol. 95, No. 2, pp. 581-582 (construction ofcyclopropyl group), and by the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-Cyclobutylphenol can be produced by the method disclosed in, forexample, German Patent DE-2825388.

1-(2-Hydroxyphenyl)cyclobutancarbonitrile can be produced by the methoddisclosed in, for example, Pharmaceutical Chemistry Journal (EnglishTranslation), 1980, vol. 14, No. 2, pp. 114-118.

1-(2-Hydroxyphenyl)cyclobutanecarboxylic acid can be produced by themethod disclosed in, for example, Pharmaceutical Chemistry Journal(English Translation), 1980, vol. 14, No. 2, pp. 114-118.

2-(1-Propynyl)phenol can be produced by the method disclosed in, forexample, Journal of the Chemical Society: Parkin transaction I, 1998,pp. 477-484.

2-(Cyclopropylmethyl)phenol can be produced in accordance with themethod disclosed in, for example, Organic Reactions, 1941, vol, 1, p.155 (Clemmensen reduction) from cyclopropyl(2-hydroxyphenyl)methanonewhich can be produced by the method disclosed in Journal of the ChemicalSociety: Parkin transaction I, 1990, pp. 689-693 from commerciallyavailable 2,3-dihydro-4H-chromen-4-one.

2-(Methoxymethyl)phenol can be produced by the method disclosed in, forexample, Tetrahedron Letters, 1999, vol. 40, p. 6049.

2-(Ethoxymethyl)phenol can be produced by the method disclosed in, forexample, Tetrahedron Letters, 1999, vol. 40, p. 6049.

2-(1,3-Dioxolan-2-yl)phenol can be produced by the method disclosed in,for example, Tetrahedron Letters, 1989, vol. 30, No. 13, pp. 1609-1612.

1-(2-Hydroxyphenyl)ethanone O-methyloxime can be produced in accordancewith the method disclosed in, for example, commercially available1-(2-hydroxyphenyl)ethanone, Journal of the American Chemical Society,1986, vol. 108, pp. 6016-6023.

3′-(Trifluoromethyl)[1,1′-biphenyl]-2-ol can be produced in accordancewith the method disclosed in, for example, from commercially available2-iodophenol and 3-(trifluoromethyl)phenylboronic acid, ChemicalReviews, 1995, vol. 95, pp. 2457-2483 (phenylation reaction,Suzuki-Miyaura coupling reaction).

2-(1H-pyrrole-1-yl)phenol can be produced by the method disclosed in,for example, The Journal of Antibiotics, 1994, vol. 47, No. 5, pp.602-605.

2-(2-Thienyl)phenol can be produced by the method disclosed in, forexample, Journal of Heterocyclic Chemistry, 1985, vol. 22, pp.1667-1669.

2-(3-Thienyl)phenol can be produced by the method disclosed in, forexample, Journal of Heterocyclic Chemistry, 1985, vol. 22, pp.1667-1669.

2-(1H-pyrazol-1-yl)phenol can be produced by the method disclosed in,for example, Canadian Journal of Chemistry, 1963, vol. 41, pp.2086-2092.

2-(3,5-Dimethyl-1H-pyrazol-1-yl)phenol can be produced by the methoddisclosed in, for example, Heterocycles, 1982, vol. 19, No. 8, pp.1487-1495.

2-[3-(Trifluoromethyl)-1H-pyrazol-1-yl]phenol can be produced, forexample, by preparing 1-(2-methoxyphenyl)-3-(trifluoromethyl)-1H-pyrazolfrom commercially available 1-(2-methoxyphenyl)hydrazine hydrochlorideby the method disclosed in Journal of Fluorine Chemistry 1998, vol. 92,p. 23, and in accordance with the method disclosed in Organic Synthesis,Collective Volume, vol. 5, pp. 412-414 (conversion of phenylmethyl etherinto phenol, demethylation reaction).

2-[4-(Trifluoromethyl)-1H-pyrazol-1-yl]phenol can be produced, forexample, by preparing1-(2-methoxyphenyl)-4-(trifluoromethyl)-1H-pyrazole from commerciallyavailable 1-(2-methoxyphenyl)hydrazine hydrochloride by the methoddisclosed in Tetrahedron Letters, 1996, vol. 37, No. 11, p. 1829, and inaccordance with the method disclosed in Organic Synthesis, CollectiveVolume, vol. 5, pp. 412-414 (conversion of phenylmethyl ether intophenol, demethylation reaction).

2-[5-(Trifluoromethyl)-1H-pyrazol-1-yl]phenol can be produced, forexample, by preparing1-(2-methoxyphenyl)-5-(trifluoromethyl)-1H-pyrazole from commerciallyavailable 1-(2-methoxyphenyl)hydrazine hydrochloride by the methoddisclosed in Journal of Fluorine Chemistry, 1998, vol. 92, p. 23, and inaccordance with the method disclosed in Organic Synthesis, CollectiveVolume, vol. 5, pp. 412-414 (conversion of phenylmethyl ether intophenol, demethylation reaction).

5-(2-Hydroxyphenyl)-N,N-dimethyl-1H-pyrazol-1-sulfonamide can beproduced, for example, from5-(5-chloro-2-hydroxyphenyl)-N,N-dimethyl-1H-pyrazol-1-sulfonamide,which can be produced from commercially available4-chloro-2-(1H-pyrazol-5-yl)phenol in accordance with the methoddisclosed in Journal of Medicinal Chemistry, 1998, vol. 41, No. 12, pp.2019-2028, in accordance with the method disclosed in, Jikken KagakuKoza (Experimental Chemistry Lecture), 4th Edition, vol. 26, pp. 251-266(catalytic hydrogenation reaction).

3-(2-Hydroxyphenyl)-N,N-dimethyl-1H-pyrazol-1-sulfonamide can beproduced, for example, from3-(5-chloro-2-hydroxyphenyl)-N,N-dimethyl-1H-pyrazol-1-sulfonamide,which can be produced from commercially available4-chloro-2-(1H-pyrazol-5-yl)phenol in accordance with the methoddisclosed in Journal of Medicinal Chemistry, 1998, vol. 41, No. 12, pp.2019-2028, in accordance with the method disclosed in, Jikken KagakuKoza (Experimental Chemistry Lecture), 4th Edition, vol. 26, pp. 251-266(catalytic hydrogenation reaction).

2-(4-Methyl-1,3-thiazol-2-yl)phenol can be produced by the methoddisclosed in, for example, from commercially available2-hydroxybenzonitrile, Japanese Provisional Patent Publication No.11-60552 (thioamidation reaction of a cyano group), and the methoddisclosed in Liebigs Annalen der Chemie, 1890, vol. 259, p. 236.

2-(1,3-Benzothiazol-2-yl)phenol can be produced by the method disclosedin, for example, The Journal of Organic Chemistry, 1970, vol. 35, pp.3147-3149.

2-(Dimethylamino)phenol can be produced by the method disclosed in, forexample, Journal of Medicinal Chemistry, 1998, vol. 41, pp. 4800-4818.

2-(2-Methoxyethoxy)phenol can be produced in accordance with the methoddisclosed in, for example, Journal of the Chemical Society: Parkintransaction I, 1980, pp. 756-758 from commercially availablepyrocatechol.

2-(Isopropylsulfanyl)phenol can be produced by the method disclosed in,for example, Tetrahedron, 1970, vol. 26, pp. 4449-4471.

3-Cyclopropylphenol can be produced by the method disclosed in, forexample, from commercially available 1-bromo-3-methoxybenzene,Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255 (construction ofcyclopropyl group, Suzuki-Miyaura coupling reaction), and in accordancewith the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

3-(2-Furyl)phenol can be produced, for example, by producing2-(3-methoxyphenyl)furan by the method disclosed in The Journal ofOrganic Chemistry, 1993, vol. 58, No. 17, pp. 4722-4726, and inaccordance with the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

4-Cyclopropylphenol can be produced in accordance with the methoddisclosed in, for example, from commercially available1-bromo-4-methoxybenzene, Tetrahedron Letters, 2000, vol. 41, pp.4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura couplingreaction), and by the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

2-Bromo-3-methylphenol can be produced in accordance with the methoddisclosed in, for example, from commercially available2-methoxy-6-methylaniline, Organic Synthesis, Collective Volume, vol. 3,pp. 185-187 or the method disclosed in The Journal of Organic Chemistry,1977, vol. 42, pp. 2426-2430 (conversion of anilines into bromobenzene,Sandmeyer reaction, etc.) and, Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

3-Fluoro-2-methylphenol can be produced in accordance with the methoddisclosed in Journal of the Chemical Society: Parkin transaction I,1974, p. 1353 from commercially available 3-fluoro-2-methylbenzaldehyde.

3-Chloro-2-methylphenol can be produced in accordance with the methoddisclosed in Organic Synthesis, Collective Volume, vol. 5, pp. 412-414(conversion of phenylmethyl ether into phenol, demethylation reaction)from commercially available 1-chloro-3-methoxy-2-methylbenzene.

3-Methoxy-2-methylphenol can be produced in accordance with the methoddisclosed in, Organic Synthesis, Collective Volume, vol. 4, pp. 836-838(conversion of phenol into phenyl methyl ether, methylation reaction)from commercially available 2-methyl-1,3-benzene diol.

2-Cyclopropyl-3-methylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available2-methoxy-6-methylaniline, Organic Synthesis, Collective Volume, vol. 3,pp. 185-187 or the method disclosed in The Journal of Organic Chemistry,1977, vol. 42, pp. 2426-2430 (conversion of anilines into bromobenzene,Sandmeyer reaction, etc.), and the method disclosed in TetrahedronLetters, 1979, vol. 20, pp. 4159-4162 or the method disclosed inTetrahedron, 1997, vol. 53, No. 43, pp. 14599-14614 or the methoddisclosed in Bulletin of the Chemical Society of Japan, 1971, vol. 44,pp. 2237-2248 (conversion reaction of aromatic bromide into aromaticaldehyde), and the method disclosed in The Journal of Organic Chemistry,1963, vol. 2.8, p. 1128 or Synthetic Communications, 1985, vol. 15, No.10, pp. 855-864 (conversion of carbonyl group into olefin, Wittgreaction), and the method disclosed in Organic Reactions, 1973, vol. 20,pp. 1-131 or Journal of the American Chemical Society, 1975, vol. 97,3428 or the method disclosed in Tetrahedron Letters, 1998, vol. 39, pp.8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction),and the method disclosed in Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

2-Cyclopropyl-3-methoxyphenol can be produced in accordance with themethod disclosed in, for example, from commercially available2,6-dimethoxybenzaldehyde, The Journal of Organic Chemistry, 1963, vol.28, p. 1128 or Synthetic Communications, 1985, vol. 15, No. 10, pp.855-864 (conversion of carbonyl group into olefin, Wittg reaction), andthe method disclosed in Organic Reactions, 1973, vol. 20, pp. 1-131 orJournal of the American Chemical Society, 1975, vol. 97, p. 3428 orTetrahedron Letters, 1998, vol. 39, pp. 8621-8624 (construction ofcyclopropyl group, Simmons-Smith reaction), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

4-indanol can be produced in accordance with the method disclosed in,for example, Organic Reactions, 1941, vol. 1, p. 155 (Clemmensenreduction) from commercially available 4-hydroxy-1-indanone.

3-methyl-4-indanol can be produced by the method disclosed in, forexample, Journal of Applied Chemistry, 1959, vol. 9, pp. 629 and 637.

1-Methyl-4-indanol can be produced by the method disclosed in, forexample, Journal of the Chemical Society, 1961, pp. 2773-2777.

2,2-Dimethyl-4-indanol can be produced by the method disclosed in, forexample, Journal of Chemical Research Miniprint, 1985, vol. 8, pp.2724-2747.

Spiro[cyclopropane-1,3′-(2′,3′-dihydro-1′H-inden-4′-ol)] can be producedin accordance with the method disclosed in, for example, fromcommercially available 2,3-dihydro-4H-chromen-4-ol, Bioorganic andMedicinal Chemistry, 1999, vol. 7, No. 12, pp. 2801-2810 (synthesis of7-hydroxy-1-indanone), and the method disclosed in Organic Synthesis,Collective Volume vol. 4, pp. 836-838 (conversion of phenol into phenylmethyl ether, methylation reaction), and the method disclosed in TheJournal of Organic Chemistry, 1963, vol. 28, p. 1128 or SyntheticCommunications, 1985, vol. 15, No. 10, pp. 855-864 (conversion ofcarbonyl group into olefin, Wittg reaction), and the method disclosed inOrganic Reactions, 1973, vol. 20, pp. 1-131 or Journal of the AmericanChemical Society, 1975, vol. 97, p. 3428 or Tetrahedron Letters, 1998,vol. 39, pp. 8621-8624 (construction of cyclopropyl group, Simmons-Smithreaction), and the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

7-hydroxy-2,3-dihydro-1H-inden-1-one O-methyloxime can be produced inaccordance with the method disclosed in, for example, from commerciallyavailable 2,3-dihydro-4H-chromen-4-ol, Bioorganic and MedicinalChemistry, 1999, vol. 7, No. 12, pp. 2801-2810 (synthesis of7-hydroxy-1-indanone), and the method disclosed in Organic Synthesis,Collective Volume vol. 4, pp. 836-838 (conversion of phenol into phenylmethyl ether, methylation reaction), and the method disclosed inChemical Pharmaceutical Bulletin, 1988, vol. 36, No. 8, pp. 3134-3137(conversion of carbonyl group into oxime), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2,3-Dihydro-1-benzofuran-4-ol can be produced by the method disclosedin, for example, Journal of the Chemical Society, 1948, p. 894(reduction of olefin) from 1-benzofuran-4-ol which is obtained by themethod disclosed in Helvetica Chimica Acta, 1933, vol. 16, pp. 121-129.

3-Methyl-2,3-dihydro-1-benzofuran-4-ol can be produced in accordancewith the method disclosed in, for example, Journal of the ChemicalSociety, 1948, p. 894 (reduction of olefin) from3-methyl-1-benzofuran-4-ol which is obtained by the method disclosed inJournal of the Chemical Society, 1951, pp. 3229-3234.

1-Benzofuran-4-ol can be produced by the method disclosed in, forexample, Helvetica Chimica Acta, 1933, vol. 16, pp. 121-129.

3-Methyl-1-benzofuran-4-ol can be produced by the method disclosed in,for example, Journal of the Chemical Society, 1951, pp. 3229-3234.

1-Benzothiophen-4-ol can be produced by the method disclosed in, forexample, Journal of the American Chemical Society, 1935, vol. 57, pp.1611-1615.

2-Methyl-1,3-benzoxazol-4-ol can be produced in accordance with themethod disclosed in, for example, Journal of Medicinal Chemistry, 1987,vol. 30, No. 1, pp. 62-67.

2,3-Dihydro-1-benzofuran-7-ol can be produced in accordance with themethod disclosed in, for example, from commercially available7-methoxy-1-benzofuran, Journal of the Chemical Society, 1948, p. 894(hydrogenation reaction of benzofuran), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

1-Benzofuran-7-ol can be produced in accordance with the methoddisclosed in, for example, from commercially available7-methoxy-1-benzofuran, Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

1,3-Benzodioxol-4-ol can be produced by the method disclosed in, forexample, Chemical Pharmaceutical Bulletin, 1981, vol. 29, No. 10, pp.2893-2898 from commercially available 1,2,3-benzene triol.

2,3-Dihydro-1,4-benzodioxyn-5-ol can be produced by the method disclosedin, for example, Journal of the Chemical Society: Parkin transaction I,1988, pp. 511 to 520 from commercially available 1,2,3-benzene triol.

2-Methyl-1,3-benzoxazol-7-ol can be produced in accordance with themethod disclosed in, for example, Liebigs Annalen der Chemie, 1957, vol.608, p. 128 (reduction of a nitro group into an amino group), and themethod disclosed in Journal of Medicinal Chemistry, 1987, vol. 30, No.1, pp. 62-67 from commercially available 3-nitro-1,2-benzene diol.

2-Bromo-4-tert-butylphenol can be produced by the method disclosed in,for example, Tetrahedron, 1999, vol. 55, No. 28, pp. 8377-8384.

2-Ethyl-4-iodophenol can be produced by the method disclosed in, TheJournal of Organic Chemistry, 1951, vol. 16, pp. 1117-1120 fromcommercially available 2-ethylphenol.

4-Bromo-2-isopropylphenol can be produced by the method disclosed in,for example, Journal of Medicinal Chemistry, 1971, vol. 14, No. 9, pp.789-792.

3-Cyclopropyl-4-methylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available2-bromo-1-methoxy-4-methylbenzene, Tetrahedron Letters, 2000, vol. 41,pp. 4251-4255 (construction of cyclopropyl group, Suzuki-Miyauracoupling reaction) and the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

5-(Dimethylamino)-2-methylphenol can be produced by the method disclosedin, for example, Journal of the Chemical Society, 1947, pp. 182-191.

5-Methoxy-2-methylphenol can be produced by the method disclosed in, forexample, Chemical Abstracts, 1938, p. 2519.

2-Ethyl-5-methoxyphenol can be produced by the method disclosed in, forexample, Chemical and Pharmaceutical Bulletin, 1979, vol. 27, No. 6, pp.1490-1494.

2,5-Diisopropylphenol can be produced by the method disclosed in, forexample, The Journal of Organic Chemistry, 1980, vol. 45, No. 22, pp.4326-4329.

2-Cyclopropyl-5-fluorophenol can be produced in accordance with themethod disclosed in, for example, from commercially available2-bromo-5-fluorophenol, Helvetica Chimica Acta, 1992, vol. 75, p. 457(conversion of phenol into phenylmethoxymethyl ether, methoxymethylationreaction), and the method disclosed in Tetrahedron Letters, 2000, vol.41, pp. 4251-4255 (construction of cyclopropyl group, Suzuki-Miyauracoupling reaction), and the method disclosed in Tetrahedron, 1998, vol.54, pp. 15861-15869 (conversion of phenylmethoxymethyl ether intophenol, demethoxymethylation reaction).

5-Chloro-2-cyclopropylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available4-chloro-2-methoxyphenol, The Journal of Organic Chemistry, 1997, vol.62, No. 2, pp. 261-274 (trifluoromethanesulfonylation of phenol), andthe method disclosed in Tetrahedron Letters, 2000, vol. 41, pp.4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura couplingreaction), and the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

2-Cyclopropyl-5-methylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available2-methoxy-4-methylphenol, The Journal of Organic Chemistry, 1997, vol.62, No. 2, pp. 261-274 (trifluoromethanesulfonylation of phenol), andthe method disclosed in Tetrahedron Letters, 2000, vol. 41, pp.4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura couplingreaction), and the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

2-Cyclopropyl-5-ethylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available4-ethyl-2-methoxyphenol, The Journal of Organic Chemistry, 1997, vol.62, No. 2, pp. 261-274 (trifluoromethanesulfonylation of phenol), andthe method disclosed in Tetrahedron Letters, 2000, vol. 41, pp.4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura couplingreaction), and the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

2-Cyclopropyl-5-isopropylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available3-isopropylphenol, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol), and the method disclosed in HelveticaChimica Acta, 1992, vol. 75, p. 457 (conversion of phenol intophenylmethoxymethyl ether, methoxymethylation reaction), and the methoddisclosed in Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255(construction of cyclopropyl group, Suzuki-Miyaura coupling reaction),and the method disclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869(conversion of phenylmethoxymethyl ether into phenol,demethoxymethylation reaction).

4-Cyclopropyl-3-hydroxybenzonitrile can be produced in accordance withthe method disclosed in, for example, from commercially available4-hydroxy-3-methoxybenzonitrile, The Journal of Organic Chemistry, 1997,vol. 62, No. 2, pp. 261-274 (trifluoromethanesulfonylation of phenol),and the method disclosed in Tetrahedron Letters, 2000, vol. 41, pp.4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura couplingreaction), and the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

5-Fluoro-2-[(1E)-1-propenyl]phenol can be produced in accordance withthe method disclosed in, for example, Journal of the Chemical Society:Parkin transaction I, 1994, pp. 1823-1831 (synthesis of4-fluoro-2-hydroxybenzaldehyde), and the method disclosed in OrganicSynthesis, Collective Volume, vol. 4, pp. 836-838 (conversion of phenolinto phenyl methyl ether, methylation reaction), and the methoddisclosed in Synthetic Communications, 1985, vol. 15, No. 10, pp.855-864 (conversion of carbonyl group into olefin, Wittg reaction), andthe method disclosed in Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

5-Chloro-2-[(1E)-1-propenyl]phenol can be produced in accordance withthe method disclosed in, for example, The Journal of Organic Chemistry,1964, vol. 29, pp. 2693-2698 (synthesis of4-chloro-2-hydroxybenzaldehyde), and the method disclosed in OrganicSynthesis, Collective Volume, vol. 4, pp. 836-838 (conversion of phenolinto phenyl methyl ether, methylation reaction), the method disclosed inSynthetic Communications, 1985, vol. 15, No. 10, pp. 855-864 (conversionof carbonyl group into olefin, Wittg reaction), and the method disclosedin Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9,pp. 1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

4-(Dimethylamino)-2-hydroxybenzaldehyde can be produced by the methoddisclosed in, for example, German Patent (DE 105103).

5-Chloro-2-methoxyphenol can be produced in accordance with the methoddisclosed in, for example, Organic Synthesis, Collective Volume, vol. 2,pp. 130-133 (conversion of anilines into chlorobenzene, Sandmeyerreaction, etc.) from commercially available 5-amino-2-methoxyphenol.

5-Bromo-2-methoxyphenol can be produced in accordance with the methoddisclosed in, for example, Organic Synthesis, Collective Volume, vol. 3,pp. 185-187 or the method disclosed in The Journal of Organic Chemistry,1977, vol. 42, pp. 2426-2430 (conversion of anilines into bromobenzene,Sandmeyer reaction, etc.) from commercially available5-amino-2-methoxyphenol.

3-Hydroxy-4-methoxybenzonitrile can be produced by the method disclosedin, for example, Synthesis, 1998, pp. 329-332 from commerciallyavailable methyl 3,4-dimethoxybenzoate.

2,5-Dimethoxyphenol can be produced by the method disclosed in, forexample, The Journal of Organic Chemistry, 1987, vol. 57, p. 4485.

2-Bromo-6-fluorophenol can be produced in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from commercially available2-fluorophenol.

2-Fluoro-6-propylphenol can be produced in accordance with the methoddisclosed in, for example, from commercially available 2-fluorophenol,Organic Reactions, 1949, vol. 2, pp. 1-48 (allyllation of phenol,Claisen transition reaction), and the method disclosed in Journal of theAmerican Chemical Society, 1951, vol. 73, pp. 4152-4156 (conversion ofan allyl group into a propyl group, hydrogenation reaction).

2-Fluoro-6-isopropylphenol can be produced in accordance with the methoddisclosed in, for example, from commercially available2-isopropyl-6-nitrophenol, Organic Synthesis, Collective Volume vol. 4,pp. 836-838 (conversion of phenol into phenyl methyl ether, methylationreaction), the method disclosed in Liebigs Annalen der Chemie, 1975,vol. 608, p. 128 (Reduction of a nitro group into an amino group), themethod disclosed in Synthesis, 1989, p. 905 (conversion reaction of anamino group into a fluorine atom), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-Cyclopropyl-6-fluorophenol can be produced in accordance with themethod disclosed in, for example, from commercially available2-fluorophenol, Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and the method disclosed in Helvetica Chemica Acta,1992, vol. 75, p. 457 (conversion of phenol into phenylmethoxymethylether, methoxymethylation reaction), and the method disclosed inTetrahedron Letters, 2000, vol. 41, pp. 4251-4255 (construction ofcyclopropyl group, Suzuki-Miyaura coupling reaction), and the methoddisclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

2-Chloro-6-iodophenol can be produced by the method disclosed in, forexample, The Journal of Organic Chemistry, 1988, vol. 53, No. 22, pp.5281-5287.

2-Chloro-6-ethylphenol can be produced by the method disclosed in, forexample, Journal of Chemical and Engineering Data, 1969, vol. 14, p.392.

2-Chloro-6-cyclopropylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available2-chlorophenol, Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and the method disclosed in Helvetica Chimica Acta,1992, vol. 75, p. 457 (conversion of phenol into phenylmethoxymethylether, methoxymethylation reaction), and the method disclosed inTetrahedron Letters, 2000, vol. 41, pp. 4251-4255 (construction ofcyclopropyl group, Suzuki-Miyaura coupling reaction), and the methoddisclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

2-Chloro-6-(2-methyl-2-propenyl)phenol can be produced in accordancewith the method disclosed in, for example, Organic Reactions, 1949, vol.2, pp. 1-48 (allylation of phenol, Claisen transition reaction) fromcommercially available 2-chlorophenol.

2-Bromo-6-methylphenol can be produced by the method disclosed in, forexample, Tetrahedron Letters, 1998, vol. 39, p. 2947.

2-Bromo-6-ethylphenol can be produced in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from commercially available2-ethylphenol.

2-Bromo-6-cyclopropylphenol can be produced in accordance with themethod disclosed in, for example, from commercially available2,6-dibromophenol, Organic Synthesis, Collective Volume vol. 4, pp.836-838 (conversion of phenol into phenyl methyl ether, methylationreaction), and the method disclosed in Tetrahedron Letters, 2000, vol.41, pp. 4251-4255 (construction of cyclopropyl group, Suzuki-Miyauracoupling reaction), and the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

3-Bromo-2-hydroxybenzonitrile can be produced in accordance with themethod disclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p.2947 (bromination reaction of phenol) from commercially available2-hydroxybenzonitrile.

2-Bromo-6-methoxyphenol can be produced by the method disclosed in, forexample, Synthesis, 1999, vol. 7, pp. 1127-1134.

2-Iodo-6-methylphenol can be produced by the method disclosed in, forexample, Australian Journal of Chemistry, 1997, vol. 50, No. 7, pp.767-770.

2-Ethyl-6-iodophenol can be produced in accordance with the methoddisclosed in, Australian Journal of Chemistry, 1997, vol. 50, No. 7, pp.767-770 (iodation reaction of phenol) from commercially available2-ethylphenol.

2-Iodo-6-isopropylphenol can be produced in accordance with the methoddisclosed in, Australian Journal of Chemistry, 1997, vol. 50, No. 7, pp.767-770 (iodation reaction of phenol) from commercially available2-isopropylphenol.

2-Isopropyl-6-methylphenol can be produced by the method disclosed in,for example, Bulletin de la Societe Chemique de France, 1962, pp.1700-1705.

2-s-Butyl-6-methylphenol can be produced by the method disclosed in, forexample, Angewandte Chemie, 1957, vol. 69, p. 699, p. 703. Also, forexample, it can be produced in accordance with the method disclosed inOrganic Reactions, 1949, vol. 2, pp. 1-48 (allylation of phenol, Claisentransition reaction), and Journal of the American Chemical Society,1951, vol. 73, pp. 4152-4156 (conversion of allyl group into propylgroup, hydrogenation reaction) from commercially available2-methylphenol.

2-Cyclopropyl-6-methylphenol can be produced from commercially available2-hydroxy-3-methylbenzaldehyde in accordance with the method disclosedin, for example, Organic Synthesis, Collective Volume, vol. 4, pp.836-838 (conversion of phenol into phenyl methyl ether, methylationreaction), and The Journal of Organic Chemistry, 1963, vol. 28, 1128 orSynthetic Communications, 1985, vol. 15, No. 10, pp. 855-864 (conversionof carbonyl group into olefin, Wittg reaction), and Organic Reactions,1973, vol. 20, pp. 1-131 or Journal of the American Chemical Society,1975, vol. 97, p. 3428 or Tetrahedron Letters, 1998, vol. 39, pp.8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction),and Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9,pp. 1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-Methoxy-6-methylphenol can be produced by the method disclosed in, forexample, Synthetic Communications, 1996, vol. 26, No. 1, pp. 49-62 fromcommercially available 1,2-dimethoxy-3-methylbenzene.

2,6-Diethylphenol can be produced by the method disclosed in, forexample, Journal of Medicinal Chemistry, 1960, vol. 2, pp. 201-212.

2-Cyclopropyl-6-ethylphenol can be produced from commercially available2-ethylphenol in accordance with the method disclosed in, for example,Tetrahedron Letters, 1998, vol. 39, p. 2947 (bromination reaction ofphenol), and Helvetica Chimica Acta, 1992, vol. 75, p. 457 (conversionof phenol into phenylmethoxymethyl ether, methoxymethylation reaction),and Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255 (construction ofcyclopropyl group, Suzuki-Miyaura coupling reaction), and Tetrahedron,1998, vol. 54, pp. 15861-15869 (conversion of phenylmethoxymethyl etherinto phenol, demethoxymethylation reaction).

2,6-Dipropylphenol can be produced by the method disclosed in, forexample, Liebigs Annalen der Chemie, 1919, vol. 418, pp. 90-91(synthesis of 2,6-diallylphenol), and Bulletin de la Societe Chemique deFrance, 1937, vol. 5, No. 4, pp. 1080-1083 (conversion of allyl groupinto propyl group, hydrogenation reaction).

3-Cyclopropyl-6-isopropylphenol can be produced in accordance with themethod disclosed in, for example, Journal of the Chemical Society:Parkin transaction I, 1980, pp. 1862-1865 (synthesis of2-hydroxy-3-isopropylbenzaldehyde), and Organic Synthesis, CollectiveVolume, vol. 4, pp. 836-838 (conversion of phenol into phenyl methylether, methylation reaction), and the method disclosed in The Journal ofOrganic Chemistry, 1963, vol. 28, p. 1128 or Synthetic Communications,1985, vol. 15, No. 10, pp. 855-864 (conversion of carbonyl group intoolefin, Wittg reaction), and the method disclosed in Organic Reactions,1973, vol. 20, pp. 1-131 or Journal of the American Chemical Society,1975, vol. 97, p. 3428 or Tetrahedron Letters, 1998, vol. 39, pp.8621-8624 (construction of cyclopropyl group, Simmons-Smith reaction),and the method disclosed in Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

3-tert-Butyl-6-cyclopropylphenol can be produced in accordance with themethod disclosed in, for example, commercially available3-tert-butyl-2-hydroxybenzaldehyde

, Organic Synthesis, Collective Volume, vol. 4, pp. 836-838 (conversionof phenol into phenyl methyl ether, methylation reaction), and themethod disclosed in The Journal of Organic Chemistry, 1963, vol. 28, p.1128 or Synthetic Communications, 1985, vol. 15, No. 10, pp. 855-864(conversion of carbonyl group into olefin, Wittg reaction), and themethod disclosed in Organic Reactions, 1973, vol. 20, pp. 1-131 orJournal of the American Chemical Society, 1975, vol. 97, p. 3428 orTetrahedron Letters, 1998, vol. 39, pp. 8621-8624 (construction ofcyclopropyl group, Simmons-Smith reaction), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2,6-Dicyclopropylphenol can be produced in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1997, vol. 38, No. 17,pp. 3111-3114 (synthesis of 2-hydroxyisophthalaldehyde), and the methoddisclosed in Organic Synthesis, Collective Volume, vol. 4, pp. 836-838(conversion of phenol into phenyl methyl ether, methylation reaction),and the method disclosed in The Journal of Organic Chemistry, 1963, vol.28, p. 1128 or Synthetic Communications, 1985, vol. 15, No. 10, pp.855-864 (conversion of carbonyl group into olefin, Wittg reaction), andthe method disclosed in Organic Reactions, 1973, vol. 20, pp. 1-131 orJournal of the American Chemical Society, 1975, vol. 97, p. 3428 orTetrahedron Letters, 1998, vol. 39, pp. 8621-8624 (construction ofcyclopropyl group, Simmons-Smith reaction), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2-Cyclopropyl-6-methoxyphenol can be produced from commerciallyavailable 2-hydroxy-3-methoxybenzaldehyde in accordance with the methoddisclosed in, for example, Helvetica Chimica Acta, 1992, vol. 75, p. 457(conversion of phenol into phenylmethoxymethyl ether, methoxymethylationreaction), and The Journal of Organic Chemistry, 1963, vol. 28, p. 1128or Synthetic Communications, 1985, vol. 15, No. 10, pp. 855-864(conversion of carbonyl group into olefin, Wittg reaction), and themethod disclosed in Organic Reactions, 1973, vol. 20, pp. 1-131 orJournal of the American Chemical Society, 1975, vol. 97, p. 3428 orTetrahedron Letters, 1998, vol. 39, pp. 8621-8624 (construction ofcyclopropyl group, Simmons-Smith reaction), and the method disclosed inTetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

2-Cyclopropyl-6-ethoxyphenol can be produced from commercially available3-ethoxy-2-hydroxybenzaldehyde in accordance with the method disclosedin, for example, Organic Synthesis, Collective Volume, vol. 4, pp.836-838 (conversion of phenol into phenyl methyl ether, methylationreaction), and the method disclosed in The Journal of Organic Chemistry,1963, vol. 28, p. 1128 or Synthetic Communications, 1985, vol. 15, No.10, pp. 855-864 (conversion of carbonyl group into olefin, Wittgreaction), and the method disclosed in Organic Reactions, 1973, vol. 20,pp. 1-131 or Journal of the American Chemical Society, 1975, vol. 97, p.3428 or Tetrahedron Letters, 1998, vol. 39, pp. 8621-8624 (constructionof cyclopropyl group, Simmons-Smith reaction), and the method disclosedin Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9,pp. 1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

2,6-Di[(1E)-1-propenyl]phenol can be produced by the method disclosedin, for example, Liebigs Annalen der Chemie, 1919, vol. 418, pp. 90-91(synthesis of 2,6-diallylphenol), and the method disclosed in Journal ofthe American Chemical Society, 1956, vol. 78, pp.1709-1713(isomerization reaction).

2,6-Diallylphenol can be produced by the method disclosed in, forexample, Liebigs Annalen der Chemie, 1919, vol. 418, pp. 90-91.

3,5-Diisopropylphenol can be produced by the method disclosed in, forexample, U.S. Patent (U.S. Pat. No. 2,790,010).

2-Bromo-3,5-dimethylphenol can be produced in accordance with the methoddisclosed in, Bulletin of the Chemical Society of Japan, 1993, vol. 66,p. 1576 (brominetion reaction of phenol) from commercially available3,5-dimethylphenol.

3,5-Dimethyl-2-propylphenol can be produced by the method disclosed in,for example, Bulletin of the Chemical Society of Japan, 1968, vol. 41,No. 3, pp. 745-746.

2-Cyclopropyl-3,5-dimethylphenol can be produced from commerciallyavailable 3,5-dimethylphenol in accordance with the method disclosed in,for example, Tetrahedron, 1998, vol. 39, p. 2947 (bromination reactionof phenol), and Organic Synthesis, Collective Volume vol. 4, pp. 836-838(conversion of phenol into phenyl methyl ether, methylation reaction),and the method disclosed in Tetrahedron Letters, 1979, vol. 20, pp.4159-4162 or the method disclosed in Tetrahedron, 1997, vol. 53, No. 43,pp. 14599-14614 or the method disclosed in Bulletin of the ChemicalSociety of Japan, 1971, vol. 44, pp. 2237-2248 (conversion reaction ofaromatic bromide into aromatic aldehyde), and the method disclosed inThe Journal of Organic Chemistry, 1963, vol. 28, p. 1128 or SyntheticCommunications, 1985, vol. 15, No. 10, pp. 855-864 (conversion ofcarbonyl group into olefin, Wittg reaction), and the method disclosed inOrganic Reactions, 1973, vol. 20, pp. 1-131 or Journal of the AmericanChemical Society, 1975, vol. 97, p. 3428 or Tetrahedron Letters, 1998,vol. 39, pp. 8621-8624 (construction of cyclopropyl group, Simmons-Smithreaction), and the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

3,5-Dimethyl-2-(methylsulfanyl)phenol can be produced by the methoddisclosed in, for example, Tetrahedron Letters, 1999, vol. 40, No. 35,pp. 6357-6358.

2-Bromo-3,6-dimethylphenol can be produced in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from commercially available3,6-dimethylphenol.

6-Bromo-3-fluoro-2-methylphenol can be produced, from3-fluoro-2-methylphenol which can be produced from commerciallyavailable 3-fluoro-2-methylbenzaldehyde in accordance with the methoddisclosed in Journal of the Chemical Society: Parkin transaction I,1974, p. 1353, in accordance with the method disclosed in, for example,Tetrahedron Letters, 1998, vol. 39, p. 2947 (bromination reaction ofphenol).

6-Bromo-3-chloro-2-methylphenol can be produced in accordance with themethod disclosed in Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from 3-chloro-2-methylphenol which canbe produced from commercially available1-chloro-3-methoxy-2-methylbenzene in accordance with the methoddisclosed in Organic Synthesis, Collective Volume, vol. 5, pp. 412-414(conversion of phenylmethyl ether into phenol, demethylation reaction).

3-Chloro-6-cyclopropyl-2-methylphenol can be produced from3-chloro-2-methylphenol which can be produced from commerciallyavailable 1-chloro-3-methoxy-2-methylbenzene in accordance with themethod disclosed in Organic Synthesis, Collective Volume, vol. 5, pp.412-414 (conversion of phenylmethyl ether into phenol, demethylationreaction), in accordance with the method disclosed in TetrahedronLetters, 1998, vol. 39, p. 2947. (bromination reaction of phenol) andHelvetica Chimica Acta, 1992, vol. 75, p. 457 (conversion of phenol intophenylmethoxymethyl ether, methoxymethylation reaction), and TetrahedronLetters, 2000, vol. 41, pp. 4251-4255 (construction of cyclopropylgroup, Suzuki-Miyaura coupling reaction), and Tetrahedron, 1998, vol.54, pp. 15861-15869 (conversion of phenylmethoxymethyl ether intophenol, demethoxymethylation reaction).

6-Bromo-2,3-dimethylphenol can be produced in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from commercially available2,3-dimethylphenol.

6-Cyclopropyl-2,3-dimethylphenol can be produced from commerciallyavailable 2,3-dimethylphenol in accordance with the method disclosed in,for example, Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and Helvetica Chimica Acta, 1992, vol. 75, p. 457(conversion of phenol into phenylmethoxymethyl ether, methoxymethylationreaction), and Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255(construction of cyclopropyl group, Suzuki-Miyaura coupling reaction),and Tetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

2-Hydroxy-3,4-dimethylbenzaldehyde O-methyloxime can be produced fromcommercially available 2,3-dimethylphenol in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol), and Helvetica Chimica Acta, 1992, vol.75, p. 457 (conversion of phenol into phenylmethoxymethyl ether,methoxymethylation reaction), and the method disclosed in TetrahedronLetters, 1979, vol. 20, pp. 4159-4162 or the method disclosed inTetrahedron, 1997, vol. 53, No. 43, pp. 14599-14614 or the methoddisclosed in Bulletin of the Chemical Society of Japan, 1971, vol. 44,pp. 2237-2248 (conversion reaction of aromatic bromide into aromaticaldehyde), and the method disclosed in Journal of the Chemical Society:Perkin transactions I, 1979, pp. 643-645 (oximation reaction), andTetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

6-Methoxy-2,3-dimethylphenol can be produced from commercially available3,4-dimethylphenol in accordance with the method disclosed in, forexample, Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol) and the method disclosed in Tetrahedron Letters,1979, vol. 20, pp. 4159-4162 or the method disclosed in Tetrahedron,1997, vol. 53, No. 43, pp. 14599-14614 or the method disclosed inBulletin of the Chemical Society of Japan, 1971, vol. 44, pp. 2237-2248(conversion reaction of aromatic bromide into aromatic aldehyde), andthe method disclosed in Journal of the Chemical Society: Parkintransaction I, 1974, p. 1353.

6-Bromo-3-methoxy-2-methylphenol can be produced in accordance with themethod disclosed in, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from 3-methoxy-2-methylphenol which canbe produced from commercially available 2-methyl-1,3-benzene diol inaccordance with the method disclosed in Organic Synthesis, CollectiveVolume, vol. 4, pp. 836-838 (conversion of phenol into phenyl methylether, methylation reaction).

6-Cyclopropyl-3-methoxy-2-methylphenol can be produced from3-methoxy-2-methylphenol which can be produced from commerciallyavailable 2-methyl-1,3-benzene diol in accordance with the methoddisclosed in Organic Synthesis, Collective Volume, vol. 4, pp. 836-838(conversion of phenol into phenyl methyl ether, methylation reaction),in accordance with the method disclosed in Tetrahedron Letters, 1998,vol. 39, p. 2947 (bromination reaction of phenol), and the methoddisclosed in Helvetica Chimica Acta, 1992, vol. 75, p. 457 (conversionof phenol into phenylmethoxymethyl ether, methoxymethylation reaction),and the method disclosed in Tetrahedron Letters, 2000, vol. 41, pp.4251-4255 (construction of cyclopropyl group, Suzuki-Miyaura couplingreaction), and the method disclosed in Tetrahedron, 1998, vol. 54, pp.15861-15869 (conversion of phenylmethoxymethyl ether into phenol,demethoxymethylation reaction).

2-Cyclopropyl-3,6-dimethylphenol can be produced from commerciallyavailable 2,5-dimethylphenol in accordance with the method disclosed in,for example, Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and the method disclosed in Organic Synthesis,Collective Volume, vol. 4, pp. 836-838 (conversion of phenol into phenylmethyl ether, methylation reaction), and the method disclosed inTetrahedron Letters, 1979, vol. 20, pp. 4159-4162 or the methoddisclosed in Tetrahedron, 1997, vol. 53, No. 43, pp. 14599-14614 or themethod disclosed in Bulletin of the Chemical Society of Japan, 1971,vol. 44, pp. 2237-2248 (conversion reaction of aromatic bromide intoaromatic aldehyde), and the method disclosed in The Journal of OrganicChemistry, 1963, vol. 28, p. 1128 or Synthetic Communications, 1985,vol. 15, No. 10, pp. 855-864 (conversion of carbonyl group into olefin,Wittg reaction), and the method disclosed in Organic Reactions, 1973,vol. 20, pp. 1-131 or Journal of the American Chemical Society, 1975,vol. 97, p. 3428 or Tetrahedron Letters, 1998, vol. 39, pp. 8621-8624(construction of cyclopropyl group, Simmons-Smith reaction), and themethod disclosed in Bioscience, Biotechnology, and Biochemistry, 1993,vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional Patent PublicationNo. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

2-Allyl-6-ethyl-3-methoxyphenol can be produced from2-ethyl-5-methoxyphenol which can be produced in accordance with themethod disclosed in Chemical and Pharmaceutical Bulletin, 1979, vol. 27,No. 6, pp. 1490-1494, in accordance with the method disclosed in, forexample, Organic Reactions, 1949, vol. 2, pp. 1-48 (allylation reactionof phenol, Claisen transition).

3,6-Dimethyl-2-[(methylsulfanyl)methyl]phenol can be produced by themethod disclosed in, for example, Journal of the American ChemicalSociety, 1966, vol. 88, No. 24, pp. 5855-5864.

5-Bromo-4-indanol can be produced in accordance with the methoddisclosed in, for example, Journal of the American Chemical Society,1946, vol. 68, p. 2487 (reduction of carbonyl group, Wolff-KishnerReduction), and Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol) from commercially available 4-hydroxy-1-indanone.

5-Methyl-4-indanol can be produced from commercially available4-hydroxy-1-indanone in accordance with the method disclosed in, forexample, Journal of the American Chemical Society, 1946, vol. 68, p.2487 (reduction of carbonyl group, Wolff-Kishner Reduction), and themethod disclosed in Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol), and the method disclosed in HelveticaChimica Acta, 1990, vol. 75, p. 457 (conversion of phenol intophenylmethoxymethyl ether, methoxymethylation reaction), and the methoddisclosed in Helvetica Chimica Acta, 1990, vol. 73, pp. 417-425(conversion reaction of bromo group into methyl group), and the methoddisclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

5-Ethyl-4-indanol can be produced from commercially available4-hydroxy-1-indanone in accordance with the method disclosed in, forexample, Journal of the American Chemical Society, 1946, vol. 68, p.2487 (reduction of carbonyl group, Wolff-Kishner Reduction), and themethod disclosed in Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol), and the method disclosed in HelveticaChimica Acta, 1992, vol. 75, p. 457 (conversion of phenol intophenylmethoxymethyl ether, methoxymethylation reaction), and the methoddisclosed in Helvetica Chimica Acta, 1990, vol. 73, pp. 417-425(conversion reaction of bromo group into ethyl group), and the methoddisclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

5-Cyclopropyl-4-indanol can be produced from commercially available4-hydroxy-1-indanone in accordance with the method disclosed in, forexample, Journal of the American Chemical Society, 1946, vol. 68, p.2487 (reduction of carbonyl group, Wolff-Kishner Reduction), and themethod disclosed in Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) and the method disclosed in OrganicSynthesis, Collective Volume, vol. 4, pp. 836-838 (conversion of phenolinto phenyl methyl ether, methylation reaction), and TetrahedronLetters, 2000, vol. 41, pp. 4251-4255 (construction of cyclopropylgroup, Suzuki-Miyaura coupling reaction), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

6-Methyl-2,3-dihydro-1-benzofuran-7-ol can be produced in accordancewith the method disclosed in, for example, Journal of the ChemicalSociety, 1948, p. 894 (reduction of olefin) from6-methyl-1-benzofuran-7-ol. 6-Methyl-1-benzofuran-7-ol can be produced,for example, from 2-methoxy-3-methylphenol which can be produced by themethod disclosed in Tetrahedron Letters, 1998, vol. 39, p. 2947, inaccordance with the method disclosed in Journal of the Chemical Society:Perkin transactions I, 1988, p. 3029 (construction of benzofuran ring),and the method disclosed in Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

6-Bromo-1-benzofuran-7-ol can be produced from commercially available7-methoxy-1-benzofuran in accordance with the method disclosed in, forexample, Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No.9, pp. 1572-1574 or Japanese Provisional Patent Publication No.11-322755 (conversion of phenylmethyl ether into phenol, demethylationreaction), and Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol).

6-Methyl-1-benzofuran-7-ol can be produced from 2-methoxy-3-methylphenolwhich can be produced by the method disclosed in Tetrahedron Letters,1998, vol. 39, p. 2947, in accordance with the method disclosed in, forexample, Journal of the Chemical Society: Perkin transactions I, 1988,p. 3029 (construction of benzofuran ring), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

6-Cyclopropyl-1-benzofuran-7-ol can be produced from commerciallyavailable 7-methoxy-1-benzofuran in accordance with the method disclosedin, for example, Bioscience, Biotechnology, and Biochemistry, 1993, vol.57, No. 9, pp. 1572-1574 or Japanese Provisional Patent Publication No.11-322755 (conversion of phenylmethyl ether into phenol, demethylationreaction), and the method disclosed in Tetrahedron Letters, 1998, vol.39, p. 2947 (bromination reaction of phenol), and the method disclosedin Helvetica Chimica Acta, 1992, vol. 75, p. 457 (conversion of phenolinto phenylmethoxymethyl ether, methoxymethylation reaction), and themethod disclosed in Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255(construction of cyclopropyl group, Suzuki-Miyaura coupling reaction),and the method disclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869(conversion of phenylmethoxymethyl ether into phenol,demethoxymethylation reaction).

2,4-Dicyclopropyl-6-fluorophenol can be produced from commerciallyavailable 2-fluorophenol in accordance with the method disclosed in, forexample, Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and Helvetica Chimica Acta, 1992, vol. 75, p. 457(conversion of phenol into phenylmethoxymethyl ether, methoxymethylationreaction), and Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255(construction of cyclopropyl group, Suzuki-Miyaura coupling reaction),and the method disclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869(conversion of phenylmethoxymethyl ether into phenol,demethoxymethylation reaction).

2,4-Dibromo-3,6-dimethylphenol can be produced in accordance with themethod disclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p.2947 (bromination reaction of phenol) from commercially available3,6-dimethylphenol.

2-Bromo-4,6-dimethylphenol can be produced in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from commercially available2,4-dimethylphenol.

2-Ethyl-4,6-diiodophenol can be produced in accordance with the methoddisclosed in, Australian Journal of Chemistry, 1997, vol. 50, No. 7, pp.767-770 (iodation reaction of phenol) from commercially available2-ethylphenol.

2-Cyclopropyl-4,6-dimethylphenol can be produced from commerciallyavailable 2,4-dimethylphenol in accordance with the method disclosed in,for example, Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and the method disclosed in Helvetica Chimica Acta,1992, vol. 75, p. 457 (conversion of phenol into phenylmethoxymethylether, methoxymethylation reaction), and the method disclosed inTetrahedron Letters, 2000, vol. 41, pp. 4251-4255 (construction ofcyclopropyl group, Suzuki-Miyaura coupling reaction), and the methoddisclosed in Tetrahedron, 1998, vol. 54, pp. 15861-15869 (conversion ofphenylmethoxymethyl ether into phenol, demethoxymethylation reaction).

2-Bromo-3,5,6-trimethylphenol can be produced in accordance with themethod disclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p.2947 (bromination reaction of phenol) from commercially available2,3,5-trimethylphenol.

5,6-Dimethyl-4-indanol can be produced from commercially available7-methyl-2H-chromen-2-one in accordance with the method disclosed in,for example, Nihon Kagakukaishi (Journal of Japan Chemical Association),1974, pp. 136-146, and the method disclosed in Organic Reactions, 1941,vol. 1, p. 155 (Clemmensen reduction).

1,2,3,5,6,7-Hexahydro-s-indacen-4-ol can be produced from commerciallyavailable indane by the method disclosed in, for example, Journal of theAmerican Chemical Society, 1977, vol. 99, pp. 8007-8014, and the methoddisclosed in Organic Reactions, 1941, vol. 1, p. 155 (Clemmensenreduction), and the method disclosed in The Journal of OrganicChemistry, 1977, vol. 42, pp. 3260-3264.

3-(1,3-Dioxolan-2-yl)phenol can be produced in accordance with themethod disclosed in, for example, Tetrahedron Letters, 1989, vol. 30,No. 13, pp. 1609-1612 from 3-hydroxybenzaldehyde.

3′-(Trifluoromethyl)[1,1′-biphenyl]-3-ol can be produced in accordancewith the method disclosed in, for example, Chemical Reviews, 1995, vol.95, pp. 2457-2483 (phenylation reaction, Suzuki-Miyaura couplingreaction) from commercially available 3-iodophenol and3-(trifluoromethyl)phenylboronic acid.

3-Hydroxy-4-methylbenzonitrile can be produced by the method disclosedin, for example, Monatshefte fur Chemie, 1957, vol. 88, pp. 228, 230.

Ethyl 3-hydroxy-4-methylbenzoate can be produced by the method disclosedin, for example, The Journal of Organic Chemistry, 1961, vol. 26, pp.1732-1734.

3-Hydroxy-4-methylbenzamide can be produced in accordance with themethod disclosed in, for example, Phosphorus and Sulfur, 1980, vol. 9,pp. 155-164 from commercially available 3-hydroxy-4-methylbenzoic acid.

3,6-Dimethyl-2-propylphenol can be produced by the method disclosed in,for example, Journal of Polymer Science, 1948, vol. 3, p. 448, p. 452.

2-Hydroxy-3,4,6-trimethylbenzaldehyde can be produced by the methoddisclosed in, for example, Liebigs Annalen der Chemie, 1906, vol. 347,p. 379.

2-Hydroxy-3,4,6-trimethylbenzaldehyde O-methyloxime can be produced inaccordance with the method disclosed in, for example, Liebigs Annalender Chemie, 1906, vol. 347, p. 379 (synthesis of2-hydroxy-3,4,6-trimethylbenzaldehyde), and in accordance with themethod disclosed in Chemical Pharmaceutical Bulletin, 1988, vol. 36, No.8, pp. 3134-3137.

2-[1-(Methoxymethyl)cyclopropyl]phenol can be produced from2-methoxy-1-(2-methoxyphenyl)ethanone which can be obtained by themethod disclosed in The Journal of Organic Chemistry, 1942, vol. 7, pp.444-456, in accordance with the method disclosed in, for example, TheJournal of Organic Chemistry, 1963, vol. 28, p. 1128 or SyntheticCommunications, 1985, vol. 15, No. 10, pp. 855-864 (conversion ofcarbonyl group into olefin, Wittig reaction), and the method disclosedin Organic Reactions, 1973, vol. 20, pp. 1-131 or Journal of theAmerican Chemical Society, 1975, vol. 97, p. 3428 or TetrahedronLetters, 1998, vol. 39, pp. 8621-8624 (construction of cyclopropylgroup, Simmons-Smith reaction), and the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-(1-Methoxycyclopropyl)phenol can be produced from1-methoxy-2-(1-methoxyvinyl)benzene which can be produced by the methoddisclosed in The Journal of Organic Chemistry, 1998, vol. 63, pp.4632-4635, in accordance with the method disclosed in, for example,Organic Reactions, 1973, vol. 20, pp. 1-131 or Journal of the AmericanChemical Society, 1975, vol. 97, p. 3428 or Tetrahedron Letters, 1998,vol. 39, pp. 8621-8624 (construction of cyclopropyl group, Simmons-Smithreaction), and the method disclosed in Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction).

2-(2-Hydroxyphenyl)cyclopropanecarbonitrile can be produced from3-(2-methoxyphenyl)acrylonitrile which can be produced by the methoddisclosed in Journal of Medicinal Chemistry, 1988, vol. 31, No. 1, pp.37-54, in accordance with the method disclosed in, for example,Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction),and the method disclosed in Helvetica Chimica Acta, 1992, vol. 75, p.457 (conversion of phenol into phenylmethoxymethyl ether,methoxymethylation reaction), and the method disclosed in The Journal ofOrganic Chemistry, 1973, vol. 38, pp. 1793-1797 or The Journal ofOrganic Chemistry, 1970, vol. 35, pp. 374-379 (cyclopropanationreaction), and the method disclosed in Tetrahedron, 1998, vol. 54, pp.15861-15869 (conversion of phenylmethoxymethyl ether into phenol,demethoxymethylation reaction).

2-(2-Ethoxycyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, The Journal of Organic Chemistry,1981, vol. 46, pp. 5143-5147 (conversion of benzyl alcohol into benzylchloride), and the method disclosed in Journal of the American ChemicalSociety, 1973, vol. 95, No. 2, pp. 581-582 (construction of cyclopropylgroup), and the method disclosed in Tetrahedron, 1998, vol. 54, pp.15861-15869 (conversion of phenylmethoxymethyl ether into phenol,demethoxymethylation reaction) from [2-(methoxymethoxy)phenyl]methanolwhich can be produced by the method disclosed in Heterocycles, 1998,vol. 48, No. 7, pp. 1373-1394.

2-(2,2-Difluorocyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, The Journal of Organic Chemistry,1973, vol. 38, pp. 1793-1797 or The Journal of Organic Chemistry, 1970,vol. 35, pp. 374-379 (cyclopropanization reaction), and the methoddisclosed in Organic Synthesis, Collective Volume, vol. 5, pp. 412-414(conversion of phenylmethyl ether into phenol, demethylation reaction)from 1-(2,2-difluorovinyl)-2-methoxybenzene which can be produced by themethod disclosed in Bulletin de la Societe Chemique de France, 1995, pp.850-856.

2-(2,2-Dichlorocyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, The Journal of Organic Chemistry,1963, vol. 28, p. 1128 or Synthetic Communications, 1985, vol. 15, No.10, pp. 855-864 (conversion of carbonyl group into olefin, Wittigreaction), and the method disclosed in Synthetic Communications, 1999,vol. 29, No. 23, pp. 4101-4112 (conversion of olefin intodichlorocyclopropane), and the method disclosed in Tetrahedron, 1998,vol. 54, pp. 15861-15869 (conversion of phenylmethoxymethyl ether intophenol, demethoxymethylation reaction) from2-(methoxymethoxy)benzaldehyde which can be produced by the methoddisclosed in Heterocycles, 1998, vol. 48, No. 7, pp. 1373-1394.

2-(2,2-Dibromocyclopropyl)phenol can be produced in accordance with themethod disclosed in, for example, from commercially available1-methoxy-2-vinylbenzene, Synthetic Communications, 1999, vol. 29, No.23, pp. 4101-4112 (using bromoform in place of chloroform. Conversion ofolefin into dibromocyclopropane), and the method disclosed in OrganicSynthesis, Collective Volume, vol. 5, pp. 412-414 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-Isopropenylphenol can be produced in accordance with the methoddisclosed in, for example, from commercially available1-(2-methoxyphenyl)ethanone, The Journal of Organic Chemistry, 1963,vol. 28, p. 1128 or Synthetic Communications, 1985, vol. 15, No. 10, pp.855-864 (conversion of carbonyl group into olefin, Wittig reaction), andthe method disclosed in Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction).

3-(2-Hydroxyphenyl)acrylonitrile can be produced in accordance with themethod disclosed in, for example, Bioscience, Biotechnology, andBiochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 or JapaneseProvisional Patent Publication No. 11-322755 (conversion of phenylmethylether into phenol, demethylation reaction) from3-(2-methoxyphenyl)acrylonitrile which can be produced by the methoddisclosed in Journal of Medicinal Chemistry, 1988, vol. 31, No. 1, pp.37-54.

2-Ethynylphenol can be produced by the method disclosed in, for example,Canadian Journal of Chemistry, 1997, vol. 75, No. 9, pp. 1256-1263 fromcommercially available 1-benzofuran.

Bicyclo[4.2.0]octa-1,3,5-trien-2-ol can be produced in accordance withthe method disclosed in, for example, Organic Reactions, 1941, vol. 1,p. 155 (Clemmensen reduction), and the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 or OrganicSynthesis, Collective Volume, vol. 5, pp. 412-414 (conversion ofphenylmethyl ether into phenol, demethylation reaction) from5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one which can be produced bythe method disclosed in The Journal of Organic Chemistry, 1982, vol. 47,pp. 2393-2396.

2-Bromo-6-chlorophenol can be produced in accordance with the methoddisclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p. 2947(bromination reaction of phenol) from commercially available2-chlorophenol.

3-Bromo-2-hydroxybenzonitrile can be produced in accordance with themethod disclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p.2947 (bromination reaction of phenol) from commercially available2-hydroxybenzonitrile.

2-(2,2-Dichlorocyclopropyl)-6-methylphenol can be produced in accordancewith the method disclosed in, for example, from commercially available2-hydroxy-3-methylbenzaldehyde, Organic Synthesis, Collective Volume,vol. 4, pp. 836-838 (conversion of phenol into phenyl methyl ether,methylation reaction), and the method disclosed in The Journal ofOrganic Chemistry, 1963, vol. 28, p. 1128 or Synthetic Communications,1985, vol. 15, No. 10, pp. 855-864 (conversion of carbonyl group intoolefin, Wittig reaction), and the method disclosed in SyntheticCommunications, 1999, vol. 29, No. 23, pp. 4101-4112 (conversion ofolefin into dichlorocyclopropane), and the method disclosed in OrganicSynthesis, Collective Volume, vol. 5, pp. 412-414 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-Methyl-6-vinylphenol can be produced in accordance with the methoddisclosed in, for example, for example, from commercially available2-hydroxy-3-methylbenzaldehyde, Organic Synthesis, Collective Volume,vol. 4, pp. 836-838 (conversion of phenol into phenyl methyl ether,methylation reaction), and the method disclosed in The Journal ofOrganic Chemistry, 1963, vol. 28, p. 1128 or Synthetic Communications,1985, vol. 15, No. 10, pp. 855-864 (conversion of carbonyl group intoolefin, Wittig reaction), and the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

6-Cyclopropyl-3-fluoro-2-methylphenol can be produced in accordance withthe method disclosed in, for example, from commercially available3-fluoro-2-methylbenzaldehyde, The Journal of Organic Chemistry, 1999,vol. 64, pp. 7921-7928 or Journal of the Chemical Society: Parkintransaction I) 1974, p. 1353 (Baeyer-Villiger oxidation, convertion ofan aromatic aldehyde into phenol), and the method disclosed inTetrahedron Letters, 1998, vol. 39, p. 2947 (bromination reaction ofphenol), and the method disclosed in Organic Synthesis, CollectiveVolume, vol. 4, pp. 836-838 (conversion of phenol into phenyl methylether, methylation reaction) and the method disclosed in TetrahedronLetters, 2000, vol. 41, pp. 4251-4255 (construction of cyclopropylgroup, Suzuki-Miyaura coupling reaction), and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

5-Methyl-1-benzofuran-4-ol can be produced from methyl4-hydroxy-1-benzofuran-5-carboxylate which can be produced by the methoddisclosed in Tetrahedron, 1995, vol. 51, pp. 4009-4022, in accordancewith the method disclosed in, for example, Organic Synthesis, CollectiveVolume, vol. 4, pp. 836-838 (conversion of phenol into phenyl methylether, methylation reaction), and the method disclosed in The Journal ofOrganic Chemistry, 2001, vol. 66, pp. 4965-4972 (reduction of ester toalcohol), and the method disclosed in Journal of Medicinal Chemistry,1999, vol. 42, No. 6, pp. 1007-1017 (conversion of benzyl alcohol intobenzylmethanesulfonyl ester), and the method disclosed in The Journal ofOrganic Chemistry, 1969, vol. 34, p. 3923 or Synthetic Communications,2001, vol. 31, No. 9, pp. 1373-1382 (reduction of halogen compound,tosylate, and mesylate), and the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

2-(2-Chloro-2-fluorocyclopropyl)phenol can be produced from2-(methoxymethoxy)benzaldehyde which can be produced by the methoddisclosed in Heterocycles, 1998, vol. 48, No. 7, pp. 1373-1394, inaccordance with the method disclosed in, for example, Journal ofFluorine Chemistry, 1983, vol. 23, pp. 339-357 (conversion of carbonylgroup into chlorofluoroolefin), and the method disclosed in The Journalof Organic Chemistry, 1973, vol. 38, pp. 1793-1797 or The Journal ofOrganic Chemistry, 1970, vol. 35, pp. 374-379 (cyclopropanationreaction), and the method disclosed in Organic Synthesis, CollectiveVolume, vol. 5, pp. 412-414 (conversion of phenylmethyl ether intophenol, demethylation reaction).

3-(Benzyloxy)phenol can be produced by the method disclosed in, forexample, The Journal of Organic Chemistry, 1997, vol. 62, No. 10, pp.3062-3075.

1-Methyl-1H-indol-4-ol can be produced in accordance with the methoddisclosed in, for example, Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction) from commercially available4-methoxy-1-methyl-1H-indole.

1-Methyl-1H-indol-7-ol can be produced in accordance with the methoddisclosed in, for example, Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction) from 7-methoxy-1-methyl-1H-indole which can beproduced by the method disclosed in Journal of Medicinal Chemistry,1992, vol. 35, No. 1, pp. 177-184.

1-(4-Hydroxy-3-methylphenyl)ethanone O-methyloxime can be produced inaccordance with the method disclosed in, for example, Journal of theAmerican Chemical Society, 1986, vol. 108, pp. 6016-6023 fromcommercially available 1-(4-hydroxy-3-methylphenyl)ethanone.

2-Isopropenyl-6-methylphenol can be produced from1-(2-hydroxy-3-methylphenyl)ethanone which can be produced by the methoddisclosed in Chemische Berichte, 1925, vol. 58, p. 41, in accordancewith the method disclosed in, for example, Organic Synthesis, CollectiveVolume, vol. 4, pp. 836-838 (conversion of phenol into phenyl methylether, methylation reaction), and the method disclosed in The Journal ofOrganic Chemistry, 1963, vol. 28, p. 1128 or Synthetic Communications,1985, vol. 15, No. 10, pp. 855-864 (conversion of carbonyl group intoolefin, Wittig reaction), and the method disclosed in Bioscience,Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp. 1572-1574 orJapanese Provisional Patent Publication No. 11-322755 (conversion ofphenylmethyl ether into phenol, demethylation reaction).

1,1-Dimethyl-5-indanol can be produced in accordance with the methoddisclosed in, for example, Organic Synthesis, Collective Volume, vol. 5,pp. 412-414 (conversion of phenylmethyl ether into phenol, demethylationreaction) from 5-methoxy-1,1-dimethylindane which can be produced by themethod disclosed in Bulletin of the Chemical Society of Japan, 2000,vol. 73, No. 12, pp. 2779-2782.

3-Bromo-6-cyclopropyl-2-methylphenol can be produced from commerciallyavailable 2-methyl-3-nitrophenol, in accordance with the methoddisclosed in Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and the method disclosed in Organic Synthesis,Collective Volume, vol. 4, pp. 836-838 (conversion of phenol into phenylmethyl ether, methylation reaction), and the modified method of themethod disclosed in Organic Synthesis, Collective Volume, vol. 1, pp.445-447 (reduction of nitrophenol to aniline; 8.5 equivalents of zincpowder and 25 equivalents of ammonium chloride are used based onnitrophenol, reaction is carried out at room temperature), and themethod disclosed in Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255(construction of cyclopropyl group, Suzuki-Miyaura coupling reaction),and the method disclosed in Organic Synthesis, Collective Volume, vol.3, pp. 185-187 or the method disclosed in The Journal of OrganicChemistry, 1977, vol. 42, pp. 2426-2430 (conversion of anilines intobromobenzene, Sandmeyer reaction, etc.) and the method disclosed inBioscience, Biotechnology, and Biochemistry, 1993, vol. 57, No. 9, pp.1572-1574 or Japanese Provisional Patent Publication No. 11-322755(conversion of phenylmethyl ether into phenol, demethylation reaction).

6-Cyclopropyl-2-methyl-3-nitrophenol can be produced from commerciallyavailable 2-methyl-3-nitrophenol, in accordance with the methoddisclosed in Tetrahedron Letters, 1998, vol. 39, p. 2947 (brominationreaction of phenol), and the method disclosed in Organic Synthesis,Collective Volume, vol. 4, pp. 836-838 (conversion of phenol into phenylmethyl ether, methylation reaction), and the modified method of themethod disclosed in Organic Synthesis, Collective Volume, vol. 1, pp.445-447 (reduction of nitrophenol to aniline; 8.5 equivalents of zincpowder and 25 equivalents of ammonium chloride are used based onnitrophenol, reaction is carried out at room temperature), and themethod disclosed in Tetrahedron Letters, 2000, vol. 41, pp. 4251-4255(construction of cyclopropyl group, Suzuki-Miyaura coupling reaction),and the method disclosed in Bioscience, Biotechnology, and Biochemistry,1993, vol. 57, No. 9, pp. 1572-1574 or Japanese Provisional PatentPublication No. 11-322755 (conversion of phenylmethyl ether into phenol,demethylation reaction), and the method disclosed in Tetrahedron, 1987,vol. 43, No. 8, pp. 1753-1758 (conversion of aniline derivative intonitrobenzene).

5-Methyl-1,3-dihydro-2-benzofuran-4-ol can be produced in accordancewith the method disclosed in, for example, Journal of the AmericanChemical Society, 2000, vol. 122, pp. 11553-11554.

2-Fluoro-3,5,6-trimethylphenol can be produced from2,3,5-trimethyl-6-nitrophenol which can be produced by the methoddisclosed in Chemische Berichte, 1922, vol. 55, p. 2384, in accordancewith the method disclosed in, for example, Organic Synthesis, CollectiveVolume, vol. 4, pp. 836-838 (conversion of phenol into phenyl methylether, methylation reaction), and the method disclosed in LiebigsAnnalen der Chemie, 1957, vol. 608, p. 128, or the method disclosed inOrganic Synthesis, Collective Volume, vol. 5, 829-833 (Reduction of anitro group into an amino group), and the method disclosed in Synthesis,1989, pp. 905-908 (conversion of aromatic amine into aromatic fluoride),and the method disclosed in Organic Synthesis, Collective Volume, vol.5, pp. 412-414 (conversion of phenylmethyl ether into phenol,demethylation reaction).

2-Chloro-3,5,6-trimethylphenol can be produced in accordance with themethod disclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p.2947 (chlorication reaction of phenol; using N-chlorosuccinimide inplace of N-bromosuccinimide) from commercially available2,3,5-trimethylphenol.

2-Iodo-3,5,6-trimethylphenol can be produced in accordance with themethod disclosed in, for example, Tetrahedron Letters, 1998, vol. 39, p.2947 (iodation reaction of phenol; using N-iodosuccinimide in place ofN-bromosuccinimide) from commercially available 2,3,5-trimethylphenol.

2-Ethyl-3,5,6-trimethylphenol can be produced in accordance with themethod disclosed in, for example, Journal of the American ChemicalSociety, 1946, vol. 68, p. 2487 (reduction of carbonyl group,Wolff-Kishner reduction) from1-(2-hydroxy-3,4,6-trimethylphenyl)ethanone which can be produced by themethod disclosed in Chemical Research in Toxicology, 1997, vol. 10, No.3, pp. 335-343.

2-Isopropenyl-3,5,6-trimethylphenol can be produced from1-(2-hydroxy-3,4,6-trimethylphenyl)ethanone which can be produced by themethod disclosed in Chemical Research in Toxicology, 1997, vol. 10, No.3, pp. 335-343, in accordance with the method disclosed in, for example,Organic Synthesis, Collective Volume, vol. 4, pp. 836-838 (conversion ofphenol into phenyl methyl ether, methylation reaction), and the methoddisclosed in The Journal of Organic Chemistry, 1963, vol. 28, p. 1128 orSynthetic Communications, 1985, vol. 15, No. 10, pp. 855-864 (conversionof carbonyl group into olefin, Wittig reaction), and the methoddisclosed in Bioscience, Biotechnology, and Biochemistry, 1993, vol. 57,No. 9, pp. 1572-1574 or Japanese Provisional Patent Publication No.11-322755 (conversion of phenylmethyl ether into phenol, demethylationreaction).

1-(2-Hydroxy-3,4,6-trimethylphenyl)ethanone can be produced by themethod disclosed in, for example, Chemical Research in Toxicology, 1997,vol. 10, No. 3, pp. 335-343.

2,3,5-Trimethyl-6-nitrophenol can be produced by the method disclosedin, for example, Chemische Berichte, 1922, vol. 55, p. 2384.

2,4-Dichloro-3,5,6-trimethylphenol can be produced in accordance withthe method disclosed in, for example, Tetrahedron Letters, 1998, vol.39, p. 2947 (chlorination reaction of phenol; using N-chlorosuccinimidein place of N-bromosuccinimide) from commercially available2,3,5-trimethylphenol.

Pentamethylphenol can be produced by the method disclosed in, forexample, Journal of the Chemical Society, 1949, p. 624.

After completion of the above-mentioned respective reaction steps, theobjective compounds of the respective steps can be collected from thereaction mixture according to the conventional manner. For example, thereaction mixture is optionally neutralized, and also, after removinginsoluble materials by filtration when insoluble materials exist, anorganic solvent which is immiscible with water is added to the mixture,and after washing with water, it can be obtained by distillation of thesolvent. The obtained desired compound can be further purified accordingto the conventional manner, if necessary, for example,recrystallization, reprecipitation or chromatography, etc.

Compound (I) of the present invention can be made a salt. These saltsare included in the present invention so long as they can be used as anagricultural and horticultural herbicide.

A salt of Compound (I) of the present invention may include, forexample, alkali metal salts such as lithium, sodium, potassium, etc.;alkaline earth metal salts such as magnesium, calcium, etc.; aluminumsalts; transition metal salts such as iron, copper, etc.; amine saltssuch as ammonium, trimethyl ammonium, triethyl ammonium, tetramethylammonium, pyridinium, etc.; inorganic mineral acid salts such ashydrochloride, sulfate, phosphate, etc.; or organic acid salts such asformate, acetate, toluenesulfonate, oxalate, etc.

When a pyridazine derivative is an acid component of the salt, the saltcan be produced by, for example, mixing the pyridazine derivative and abase in the presence or absence of a solvent, and removing the solvent.

The base to be used is not specifically limited so long as it is a basegenerally showing a pH 8 or more, and for example, it may be alkalimetal hydroxides such as sodium hydroxide, potassium hydroxide, etc.;alkali metal carbonates such as sodium carbonate, potassium carbonate,cesium carbonate, etc.; metal alkoxides such as sodium methoxide, sodiumethoxide, potassium t-butoxide, etc.; alkali metal salts of an organicacid such as sodium acetate, potassium acetate, sodium formate,potassium formate, etc.; alkali metal hydrides such as sodium hydride,potassium hydride, etc.; alkali metals such as sodium, potassium, etc.;aliphatic tertiary amines such as triethylamine, tributylamine,diisopropylethylamine, etc.; aliphatic cyclic tertiary amines such as1,4-diazabicyclo-[2.2.2]octane (DABCO),1,8-diazabicyclo[5.4.0]undece-7-ene (DBU), etc.; pyridines such aspyridine, collidine, 4-(N,N-dimethylamino)pyridine, etc.; metal amidessuch as lithium amide, sodium amide, etc.; or organometallic bases suchas butyl lithium, s-butyl lithium, lithium diisopropylamide, sodiumbis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, etc.

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, for example, water; alcohols such as methanol, ethanol,t-butanol, etc.; ketones such as acetone, methyl isobutyl ketone, etc.;nitriles such as acetonitrile, etc.; esters such as ethyl acetate, etc.;halogenated hydrocarbons such as methylene chloride, chloroform,dichloroethane, etc.; ethers such as diethyl ether, tetrahydrofuran,dioxane, etc.; aromatic hydrocarbons such as toluene, etc.; amides suchas dimethylformamide, dimethylacetamide, etc.; sulfoxides such asdimethylsulfoxide, etc.; or a mixed solvent of the above.

When the pyridazine derivative is a base component of a salt, the saltcan be prepared by, for example, mixing the pyridazine derivative and anacid in the presence or absence of a solvent, and removing the solvent.

The acid to be used is not specifically limited so long as it is an acidgenerally showing a pH of 6 or less, and for example, it may beinorganic mineral acids such as hydrochloric acid, hydrobromic acid,sulfuric acid, nitric acid, phosphoric acid, etc.; or organic acids suchas formic acid, acetic acid, toluenesulfonic acid, oxalic acid, benzoicacid, etc.

The solvent to be used is not specifically limited so long as it doesnot inhibit the reaction, and dissolves starting material(s) with acertain extent, for example, water; alcohols such as methanol, ethanol,t-butanol, etc.; ketones such as acetone, methyl isobutyl ketone, etc.;nitriles such as acetonitrile, etc.; esters such as ethyl acetate, etc.;halogenated hydrocarbons such as methylene chloride, chloroform,dichloroethane, etc.; ethers such as diethyl ether, tetrahydrofuran,dioxane, etc.; aromatic hydrocarbons such as toluene, etc.; amides suchas dimethylformamide, dimethylacetamide, etc.; sulfoxides such asdimethylsulfoxide, etc.; or a mixed solvent of the above.

The composition of the present invention shows herbicidal activityagainst various kinds of weeds which cause problems in a paddy field,for example, broad-leaved weeds such as Lindernia spp., Vandelliaangustifolia Benth., Rotala indica, Elatine triandra, Dopatirum junceum(Roxb.) Hamilt, Ammannia coccinea (Rottb.), Monochoria vaginaris, etc.;Cyperaceous weeds such as smallflower umbrella sedge, Scirpus juncoides,needle spikerush, Cyperus serotinus, Scirpus nipponicus Makino etc.; andArrowhead plant weeds such as Sagittaria pygmaea, arrowhead, Alismacanaliculatum, and shows no crop injury, which causes any problem, torice.

The composition of the present invention shows herbicidal activitiesboth by foliar application and soil application against valious kinds ofweeds, which are troublesome in upland fields, including, for example,broad-leaved weeds such as Common purslane, Common chickweed, Commonlambsquarters, Amaranthus retroflexus L.i, Sinapis arvensis,shepherdspurse, velvetleaf, Sida spinosa, field pansy, Cleavers, Lamiumpurpureum, henbit, Datura stramonium L., Solanum nigrum L., Persianspeedwell, Matricaria indora, etc.; Commelinaceae weeds such as asiaticdayflower; and Cyperaceous weeds such as Cyperus iria, Cyperus rotundus,etc., and shows no crop injury which causes a problem, against corn,wheat, soybean, etc.

The composition of the present invention can be used not only in anupland and a paddy field, but also in an orchard, a mulberry field and anon-crop land.

Synergistic effects of the present invention can be admitted in a widerange of a mixing ratio, and when the second herbicidally activecompound is Compound A, B or C, the second herbicidally active compoundis mixed with a ratio of, in general, 0.1 to 50 parts by weight based on1 part by weight of Compound (I) to prepare a useful herbicidalcomposition, and the ratio is preferably 0.2 to 20 parts by weight, morepreferably 0.5 to 10 parts by weight, and when the second herbicidallyactive compound is Compound D, E, F or G, the second herbicidally activecompound is mixed with a ratio of, in general, 0.01 to 100 parts byweight based on 1 part by weight of Compound (I) to prepare a usefulherbicidal composition, and the ratio is preferably 0.02 to 50 parts byweight, more preferably 0.1 to 10 parts by weight. The thus accomplishedherbicidal composition of the present invention gives high herbicidaleffects by applying it before germination of weeds and subjecting to asoil treatment or a foliar treatment after germination.

In the present invention, 3-phenoxy-4-pyridazinol derivatives and thesecond herbicidally active compound may be mixed and spread as apreparation, may be spread simultaneously without mixing both effectiveingredients, or may be spread one of these effective ingredients firstlyand then spread the remaining effective ingredient later. Also, an orderof spreading may be optional.

The composition of the present invention may be spread a raw materialitself, or may be used by mixing with a carrier and, if necessary, withthe other auxiliaries, and prepared in a preparation form which isgenerally used as a herbicidal composition, for example, dust powder,coarse dust powder, fine dust powder, granules, wettable powder,emulsifiable concentrate, aqueous suspension, water dispersiblegranules, suspension concentrate in water or oil, Jumbo (Throw-inPacked) formulation, etc.

The compound of the present invention is used by mixing with a carrierand, if necessary, with the other auxiliaries (a surfactant, etc.), andprepared in a preparation form which is generally used as a herbicidalcomposition, for example, dust powder, coarse dust powder, granules,fine granules, wettable powder, water-soluble agent, emulsifiableconcentrate, liquid agent, etc. The carrier herein mentioned means asynthetic or natural inorganic or organic substance which is mixed inthe herbicidal composition to aid reachability of the effectiveingredient compound to plants or to make storage, transportation orhandling of the effective ingredient easy.

A suitable solid carrier may be, for example, clays represented bykaolinite group, montmorllironite group, attapulgite group, etc.;inorganic substances such as talc, mica, pyrophyllite, pumice,vermiculite, gypsum, dolomite, diatomaceous earth, magnesium lime,phosphorus lime, zeolite, silicic acid anhydride, synthetic calciumsilicate, kaolin, bentonite, calcium carbonate, etc.; vegetable organicsubstances such as soybean powder, tobacco powder, walnut powder, wheatflour, wood powder, starch powder, crystalline cellulose, etc.;synthetic or natural polymer compounds such as coumarone resin,petroleum resin, alkyd resin, polyvinyl chloride, polyalkylene glycol,ketone resin, ester gum, copal gum, dammar gum, etc.; waxes such ascarnauba wax, paraffin wax, bees wax, etc.; or urea.

Suitable liquid carriers may include, for example, paraffin series ornaphthene series hydrocarbons such as kerosine, mineral oil, spindleoil, white oil, etc.; aromatic hydrocarbons such as benzene, toluene,xylene, ethylbenzene, cumene, methylnaphthalene, etc.; chlorinatedhydrocarbons such as carbon tetrachloride, chloroform,trichloroethylene, monochlorobenzene, chlorotoluene, etc.; ethers suchas dioxane, tetrahydrofuran, etc.; ketones such as acetone,methylethylketone, diisobutylketone, cyclohexanone, acetophenone,isophorone, etc.; esters such as ethyl acetate, amyl acetate, ethyleneglycol acetate, diethylene glycol acetate, dibutyl maleate, diethylsuccinate, etc.; alcohols such as methanol, hexanole, ethylene glycol,diethylene glycol, cyclohexanol, benzyl alcohol, etc.; ether alcoholssuch as ethylene glycol ethyl ether, ethylene glycol phenyl ether,diethylene glycol ethyl ether, diethylene glycol butyl ether, etc.;polar solvents such as dimethylformamide, dimethylsulfoxide, etc.; orwater.

A surfactant which is used for the purpose of emulsification,dispersion, wetting, spreading, binding, controlling disintegration,stabilization of effective ingredient(s), improvement in fluidity,antirust, promotion of absorption into plants, etc., may be ionic ornonionic one.

Suitable nonionic surfactants may include, for example, sucrose ester ofaliphatic acid, ethylene oxide polymerized adducts of higher fatty acidssuch as lauryl alcohol, stearyl alcohol, oleyl alcohol, etc., ethyleneoxide polymerized adducts of alkylphenols such as isooctylphenol,nonylphenol, etc., ethylene oxide polymerized adducts of alkyl naphtholsuch as butylnaphthol, octylnaphthol, etc., ethylene oxide polymerizedadducts of higher fatty acids such as palmitic acid, stearic acid, oleicacid, etc., ethylene oxide polymerized adducts of mono- ordialkylphosphates such as stearyl phosphate, dilauryl phosphate, etc.,ethylene oxide polymerized adducts of higher fatty amines such asdodecylamine, stearic amide, etc., higher fatty acid esters ofpolyvalent alcohols such as sorbitan, etc. and their ethylene oxidepolymerized adducts and copolymers of ethylene oxide and propyleneoxide, and the like.

Suitable anionic surfactants may include, for example, alkylsulfuricacid ester salts such as sodium lauryl sulfate, oleyl alcohol sulfuricacid ester amine salt, etc., aliphatic acid salts such as sodiumsulfosuccinate dioctyl ester, sodium oleate, sodium stearate, etc.,alkylarylsulfonic acid salts such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalene sulfonate, sodiumlignosulfonate, sodium dodecylbenzenesulfonate, etc.

Suitable cationic surfactants may include, for example, higher aliphaticamines, quaternary ammonium salts, alkylpyridinium salts, etc.

Moreover, in the herbicide of the present invention,

A surfactant which is used for the purpose of emulsification,dispersion, wetting, spreading, binding, controlling disintegration,stabilization of effective ingredient(s), improvement in fluidity,antirust, promotion of absorption into plants, etc., may be ionic ornonionic one.

Suitable nonionic surfactants may include, for example, sucrose ester ofaliphatic acid, ethylene oxide polymerized adducts of higher fatty acidssuch as lauryl alcohol, stearyl alcohol, oleyl alcohol, etc., ethyleneoxide polymerized adducts of alkylphenols such as isooctylphenol,nonylphenol, etc., ethylene oxide polymerized adducts of alkyl naphtholsuch as butylnaphthol, octylnaphthol, etc., ethylene oxide polymerizedadducts of higher fatty acids such as palmitic acid, stearic acid, oleicacid, etc., ethylene oxide polymerized adducts of mono- ordialkylphosphates such as stearyl phosphate, dilauryl phosphate, etc.,ethylene oxide polymerized adducts of higher fatty amines such asdodecylamine, stearic amide, etc., higher fatty acid esters ofpolyvalent alcohols such as sorbitan, etc. and their ethylene oxidepolymerized adducts and copolymers of ethylene oxide and propyleneoxide, and the like.

Suitable anionic surfactants may include, for example, alkylsulfuricacid ester salts such as sodium lauryl sulfate, oleyl alcohol sulfuricacid ester amine salt, etc., aliphatic acid salts such as sodiumsulfosuccinate dioctyl ester, sodium oleate, sodium stearate, etc.,alkylarylsulfonic acid salts such as sodium isopropylnaphthalenesulfonate, sodium methylenebisnaphthalene sulfonate, sodiumlignosulfonate, sodium dodecylbenzenesulfonate, etc.

Suitable cationic surfactants may include, for example, higher aliphaticamines, quaternary ammonium salts, alkylpyridinium salts, etc.

Moreover, in the herbicide of the present invention, for the purpose ofimproving characteristics of the preparation and heightening biologicaleffects, for example, polymer compounds such as gelatin, Gum Arabic,caseine, albumin, glue, sodium arginate, polyvinyl alcohol,carboxymethyl cellulose, methyl cellulose, hydroxymethyl cellulose,etc., thixotropic agents such as sodium polyphosphate, bentonite, etc.and other auxiliaries may be contained as other components.

Dust powder or crude dust powder generally contains, for example, 0.1 to25 parts by weight of an effective ingredient, and the reminder is asolid carrier.

Wettable powder or granular wettable powder generally contains, forexample, 1 to 90 parts by weight of an effective ingredient, and thereminder is a solid carrier and a dispersing or wetting agent, and aprotective colloidal agent, thixotropic agent and defoaming agent areadded depending on necessity. These preparations are suspended anddispersed when they are thrown into water and stirred.

Granules or fine dust powder generally contain(s), for example, 0.1 to35 parts by weight of an effective ingredient, and the reminder is asolid carrier in almost all the part. The effective ingredient compoundis uniformly mixed with a solid carrier, or firmly fixed or adsorbed onthe surface of the solid carrier, and a size of the grain is generally0.2 to 1.5 mm.

Emulsifiable concentrate generally contains, for example, 1 to 70 partsby weight of an effective ingredient compound, and further 5 to 20 partsby weight of an emulsifying agent is contained therein, and the reminderis a liquid carrier, and other auxiliaries such as a rust proof agent,etc. may be added if necessary.

Aqueous suspension or oil suspension is one in which the effectiveingredient is suspended or emulsified and dispersed in water or anorganic solvent with a high boiling point by using a suitablesurfactant, and stability with a lapse of time is maintained by adding athickening agent, etc., if necessary.

The Jumbo (Throw-in Packed) formulation can be prepared by making anactive ingredient suitable preparation forms, for example, dust powder,granule, tablet, emulsifiable concentrate, clumpy tablet, etc., and ifnecessary, they are dividedly packed in a water-soluble film or acontainer, and at the time of use, they are directry thrown into a paddyfield with several to several hundred preparations.

The compound of the present invention thus prepared in various types offormulations may be applied, for example, at dosage of 1 g to 1000 g,preferably 10 g to 300 g of an active ingredient per 10 are when it issubjected to soil treatment in a paddy field before or after germinationof weeds, whereby weeds can be effectively eliminated.

As a method for treating the compound of the present invention, it canbe applied, generally by preparing a formulation, as a soil treatment, afoliar treatment or a submerged treatment at pre-emergence orpost-emergence within about one month after germination of weeds. In thesoil treatment, there are soil surface treatment, soil incorporation,etc., in the foliar treatment, in addition to a treatment from upward ofa plant canopy, there is a directed treatment in which weeds alone aretreated so that the compound is not adhered to crops, etc., and in thesubmerged treatment, there are spreading or injection treatment ofgranules or flowable agent to water surface, etc.

Into the herbicidal composition of the present invention, otherherbicides may be added to broaden weeding spectrum.

The herbicidal composition of the present invention can be used bymixing with, for example, a plant growth regulator, fungicide,insecticide, acaricide, nematocide or fertilizer, etc.

BEST MODE FOR CARRYING OUT THE INVENTION

In the following, Examples, Preparation examples and Test examples ofthe present invention are shown to explain the invention morespecifically, but the present invention is not limited by these.Incidentally, in the following Preparation examples, “%” means % byweight.

EXAMPLE 1 6-Chloro-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 128)(1) 3-Chloro-6-(2-methylphenoxy)pyridazine (Step A-1)

A mixture of 278.7 g (1.87 mol) of 3,6-dichloropyridazine, 202.3 g (1.87mol) of 2-methylphenol and 259 g (1.87 mol) of potassium carbonate wasstirred at 160° C. for 6 hours. The reaction mixture was cooled to 70°C. and 2 L of ethyl acetate was added. This mixture was washedsuccessively with 1 mol/L sodium hydroxide aqueous solution (4×500 mL),water (4×500 mL) and brine (50 mL), and dried over anhydrous magnesiumsulfate. The solvent was removed, and isopropyl ether was added to theresidue to form crystal. The crystal was collected by filtration toobtain 234.2 g (1.06 mol, Yield: 56.7%) of3-chloro-6-(2-methylphenoxy)pyridazine.

(2) 4,6-Dichloro-3-(2-methylphenoxy)pyridazine (Step A-2)

In phosphorus oxychloride (1.85 L) was dissolved6-chloro-3-(2-methylphenoxy)pyridazine (234.2 g, 1.06 mol) obtained in(1), and 76.7 g (1.08 mol) of a chlorine gas was passed into thesolution over 4 hours. A nitrogen gas was passed into the reactionmixture to remove excess chlorine gas, and then phosphorus oxychloridewas removed. The residue was dissolved in ethyl acetate (1.5 L), washedsuccessively with water (4×500 mL) and brine(200 mL), and dried overanhydrous magnesium sulfate. The solvent was removed, and the resultingresidue was washed with 500 mL of hexane to obtain 193.1 g of a crudeproduct. This crude product was recrystallized form a mixed solvent ofhexaneethyl acetate (400 mL-240 mL) to obtain 114.4 g (0.448 mol, Yield:42.3%) of 4,6-dichloro-3-(2-methylphenoxy)pyridazine.

(3) 6-Chloro-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 128, StepA-3)

In 1,4-dioxane (1 L) was dissolved 100.0 g (0.392 mol) of4,6-dichloro-3-(2-methylphenoxy)pyridazine obtained in (2), and to thesolution were added an aqueous solution (400 mL of water) containingsodium hydroxide (purity 96%, 19.6 g, 0.470 mol) and 1.09 g (4.78 mmol)of tetrabutylammonium chloride, and the resulting mixture was stirredfor 4 hours under reflux. The reaction mixture was concentrated underreduced pressure, and the total amount was made about 100 mL. To theresidue were added an aqueous sodium hydroxide solution (13.1 g ofsodium hydroxide was dissolved in 1.4 L of water) and 500 mL of ethylacetate. The aqueous layer was washed with ethyl acetate (3×200 mL),cooled in an ice-bath, and then conc. hydrochloric acid was added toadjust the pH thereof to 5. Precipitated solid was collected by suctionfiltration, washed with 1 L of water and air dried. The resulting solidwas recrystallized from acetonitrile to obtain 34.4 g (0.145 mol, Yield:37.0%) of 6-chloro-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 128).Also, the organic layer was dried over magnesium sulfate, and thesolvent was removed. The obtained residue was purified by silica gelcolumn chromatography (YMC GEL, SIL60, 350/250 mesh, hexane-ethylacetate, gradient) to obtain 13.5 g (0.0414 mol, Yield: 10.5%) of6-chloro-3,4-bis(2-methylphenoxy)pyridazine.

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.35-7.08 (4H, m), 6.84 (1H, brs), 2.11(3H, s). Melting point (° C.): 211-213.

EXAMPLE 2 3-(2-Methylphenoxy)-4-pyridazinol (Compound No. 5) (1)6-Chloro-4-methoxy-3-(2-methylphenoxy)pyridazine (Step A-3)

In methanol (60 mL) was dissolved 3.00 g (11.8 mmol) of4,6-dichloro-3-(2-methylphenoxy)pyridazine obtained in Example 1 (2),1.00 g (17.6 mmol) of 95% sodium methoxide was added to the solution atroom temperature and the mixture was stirred at 60° C. for 4 hours.Moreover, 1.00 g (17.6 mmol) of 95% sodium methoxide was further addedand after stirring the mixture at 60° C. for 1 hour, it was allowed tostand at room temperature overnight. The reaction mixture wasconcentrated, ethyl acetate was added to the residue, and the mixturewas successively washed with water and brine. After drying overanhydrous sodium sulfate, the solvent was removed, and the obtainedresidue was purified by silica gel column chromatography (eluted withhexane:ethyl acetate=4:1) to obtain 2.75 g (11.0 mmol, Yield: 93.2%) of6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine.

(2) 4-Methoxy-3-(2-methylphenoxy)pyridazine (Step N-1)

In methanol (40 mL) was dissolved 2.00 g (7.98 mmol) of6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in (1), 0.20 gof 5% palladium-carbon was added to the solution and the mixture wasstirred under hydrogen atmosphere (1 atm) for 4 hours. The reactionmixture was filtered through Celite, and the filtrate was concentrated.The residue was purified by silica gel column chromatography (elutedwith ethyl acetate and then dichloromethane: methanol=5:1) to obtain1.59 g (7.36 mmol, Yield: 92.2%) of4-methoxy-3-(2-methylphenoxy)pyridazine.

(3) 3-(2-Methylphenoxy)-4-pyridazinol (Compound No. 5, Step N-2)

A mixture comprising 1.08 g (5.00 mmol) of4-methoxy-3-(2-methylphenoxy)pyridazine obtained in (2), 0.24 g (6.0mmol) of sodium hydroxide, water (5 mL) and 1,4-dioxane (5 mL) wasstirred overnight. The reaction mixture was washed with ethyl acetate,the aqueous layer was made acidic with hydrochloric acid, and extractedwith ethyl acetate. The solvent was removed to obtain 0.21 g (10 mmol,Yield: 20%) of 3-(2-methylphenoxy)-4-pyridazinol (Compound No. 5).

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 8.30 (1H, d, J=7.2 Hz), 7.43-7.00 (5H,m), 6.43 (1H, d, J=7.2 Hz), 2.18 (3H, s). Melting point (° C.): 169-171.

EXAMPLE 3 5-Chloro-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 45)(1) 4,5-Dichloro-3-(2-methylphenoxy)pyridazine

16.4 g (88.2 mmol) of 3-(2-methylphenoxy)pyridazine {which can beproduced by the method described in Agricultural and BiologicalChemistry, 1968, vol. 32, p. 1376 and Agricultural and BiologicalChemistry, 1969, vol. 33, p. 96.} and phosphorus oxychloride (200 mL)were mixed, the mixture was heated to 80° C., and 8.5 g (120 mmol) of achlorine gas was introduced therein. Phosphorus oxychloride was removedfrom the reaction mixture by distillation, the residue was poured intoice-cold water, and extracted with ethyl acetate. The organic layerswere combined, washed with water, and dried over anhydrous sodiumsulfate. The solvent was removed, and the residue was purified by silicagel column chromatography (available from Merck Co., 9385, hexane:ethylacetate gradient) to obtain 6.61 g (25.9 mmol, Yield: 29.4%) of4,5-dichloro-3-(2-methylphenoxy)pyridazine, 8.14 g (36.9 mmol, Yield:41.8%) of 5-chloro-3-(2-methylphenoxy)pyridazine and 1.20 g (5.44 mmol,Yield: 6.17%) of 4-chloro-3-(2-methylphenoxy)pyridazine.

(2) 5-Chloro-4-methoxy-3-(2-methylphenoxy)pyridazine (Step A-3)

5.10 g (20.0 mmol) of 4,5-dichloro-3-(2-methylphenoxy)pyridazineobtained in (1) and methanol (70 mL) were mixed, and 0.46 g (20 mmol) ofsodium was added to the mixture at −8° C., and the resulting mixture wasstirred at −8° C. for 30 minutes, and in an ice bath for 8 hours and 30minutes. Ice-cold water was added to the reaction mixture, pH was made 3with hydrochloric acid, and then the mixture was extracted with ethylacetate. The organic layers were combined, washed with water, and driedover anhydrous sodium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (available from MerckCo., 9385, hexane:ethyl acetate, gradient) to obtain 1.15 g (4.58 mmol,Yield: 22.9%) of 5-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine and3.27 g (13.0 mmol, Yield: 65%) of4-chloro-5-methoxy-3-(2-methylphenoxy)pyridazine.

(3) 5-Chloro-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 45, StepA-4, etc.)

750 mg (2.99 mmol) of 5-chloro-4-methoxy-3-(2-methylphenoxy)pyridazineobtained in (2), 156 mg (3.9 mmol) of sodium hydroxide, 1,4-dioxane (5mL) and water (10 mL) were mixed, and the mixture was refluxed withstirring for 2 hours and 30 minutes. The reaction mixture was pouredinto ice-cold water, and made acidic with hydrochloric acid. Theprecipitated solid was collected by filtration, and washed with waterand then with hexane. 525 mg (2.22 mmol, Yield: 74.2%) of5-chloro-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 45) wasobtained.

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 8.68 (1H, s), 7.38-6.80 (4H, m), 5.32(1H, brs), 2.13 (3H, s). Melting point (° C.): 238-243.

EXAMPLE 4 5-Chloro-3-(2-methylphenoxy)-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 66, Step I-1)

237 mg (1.00 mmol) of 5-chloro-3-(2-methylphenoxy)-4-pyridazinol(Compound No. 45) obtained in Example 3 and acetonitrile (8 mL) weremixed, and 112 mg (1.00 mmol) of 1,4-diazabicyclo[2,2,2]octane was addedto the mixture with stirring, and then, 191 mg (1.00 mmol) of4-methylbenzene sulfonyl chloride was added thereto, and the resultingmixture was stirred at room temperature for 1 hour and 30 minutes. Waterwas added to the reaction mixture, the mixture was made acidic withhydrochloric acid, and extracted with ethyl acetate. The organic layerswere combined, washed with water, and dried over anhydrous sodiumsulfate. The solvent was removed, and the residue was purified by silicagel column chromatography (Wako gel C-100, hexane:ethyl acetate=3:1) toobtain 379 mg (0.969 mmol, Yield: 96.9%) of5-chloro-3-(2-methylphenoxy)-4-pyridazinyl 4-methylbenzene sulfonate(Compound No. 66).

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.80 (1H, s), 7.77-6.75 (8H, m), 2.47 (3H,s), 1.98 (3H, s). Melting point (° C.): 140-143.

EXAMPLE 5 6-Chloro-3-(2-methylphenoxy)-4-pyridazinol 1-oxide (CompoundNo. 129, Step F-1)

135 mg (0.572 mmol) of 6-chloro-3-(2-methylphenoxy)-4-pyridazinol(Compound No. 128) obtained in Example 1 and methylene chloride (6 mL)were mixed, 247 mg (purity 80%, 1.14 mmol) of m-chloroperbenzoic acidwas added to the mixture and the resulting mixture was refluxed for 16hours with stirring. The mixture was allowed to stand at roomtemperature for 2 days, the reaction mixture was poured in a saturatedaqueous sodium sulfite solution, and washed with methylene chloride. Theaqueous layer was made acidic with hydrochloric acid, extracted withmethylene chloride, then washed with brine, and dried over anhydroussodium sulfate. The solvent was removed, and the obtained residue waspurified by silica gel column chromatography (YMC GEL, SIL60, 350/250mesh, eluted with ethyl acetate) to obtain 32.6 mg (0.129 mmol, Yield:22.6%) of 6-chloro-3-(2-methylphenoxy)-4-pyridazinol 1-oxide (CompoundNo. 129).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.34 (1H, s), 7.34-7.10 (4H, m), 2.20(3H, s). Melting point (° C.): 194-196.

EXAMPLE 6 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinol (Compound No.139) (1) Mixture of 6-chloro-3-(2-cyclopropylphenoxy)pyridazine 1-oxideand 3-chloro-6-(2-cyclopropylphenoxy)pyridazine 1-oxide (Step B-2)

25.3 g (189 mmol) of 2-cyclopropylphenol, 1,4-dioxane (120 mL) anddimethylsulfoxide (120 mL) were mixed, 23.2 g (207 mmol) of potassiumtert-butoxide was added to the mixture in an ice bath and the resultingmixture was stirred for 10 minutes. To the mixture was added 32.0 g (194mmol) of 3,6-dichloropyridazine 1-oxide which is a known compound, andthe mixture was allowed to stand at room temperature for 5 days. Thereaction mixture was poured into ice-cold water, and extracted withethyl acetate. The organic layers were combined, washed successsivelywith water and brine, and dried over anhydrous sodium sulfate. Thesolvent was removed, and the residue was purified by silica gel columnchromatography (hexane:ethyl acetate, gradient) to obtain 43.3 g (165mmol, Yield: 87.3%) of a mixture of6-chloro-3-(2-cyclopropylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropylphenoxy)pyridazine 1-oxide.

(2) 4,6-Dichloro-3-(2-cyclopropylphenoxy)pyridazine (Step B-3)

43.3 g (165 mmol) of a mixture of6-chloro-3-(2-cyclopropylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropylphenoxy)pyridazine 1-oxide obtained in (1),chloroform (30 mL) and 18.0 mL (194 mmol) of phosphorus oxychloride weremixed, and the mixture was heated to 60° C. and dissolved. The solutionwas stirred at room temperature overnight, and concentrated. The residuewas purified by silica gel column chromatography (hexane:ethyl acetate,gradient) to obtain 32.5 g (116 mmol, Yield: 70.3%) of4,6-dichloro-3-(2-cyclopropylphenoxy)pyridazine.

(3) 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinol (Compound No. 139,Step B-4)

In dimethylsulfoxide (500 mL) was dissolved 32.5 g (116 mmol) of4,6-dichloro-3-(2-cyclopropylphenoxy)pyridazine obtained in (2), 84 mL(210 mmol) of 10% (w/v) aqueous sodium hydroxide solution was added tothe solution, and the mixture was stirred at room temperature overnight.The reaction mixture was poured into ice-cold 1 mol/L aqueous sodiumhydroxide solution, and washed with ether. The aqueous layer was madeacidic with hydrochloric acid, the precipitated solid was collected byfiltration, and washed with water. To the resulting solid was addedacetonitrile and the mixture was heated. The mixture was cooledovernight by allowing to stand, and crystals (14.04 g) were collected byfiltration. The filtrate was concentrated, the residue wasrecrystallized from ethanol to obtain 2.64 g of crystals. These crystalswere combined to obtain 16.7 g (63.5 mmol, Yield: 54.7%) of6-chloro-3-(2-cyclopropylphenoxy)-4-pyridazinol (Compound No. 139).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.28-6.97 (4H, m), 6.82 (1H, s),1.89-1.77 (1H, m), 0.87-0.73 (2H, m), 0.73-0.58 (2H, m). Melting point(° C.): 229-231.

EXAMPLE 7 6-Chloro-3-[2-(1-fluorocyclopropyl)phenoxy]-4-pyridazinol(Compound No. 140) (1) 2-(Methoxymethoxy)benzaldehyde

In N,N-dimethylformamide (20 mL) was dissolved 5.01 g (41.1 mmol) ofcommercially available salicylaldehyde, 1.80 g (45.0 mmol) of 60% sodiumhydride was added to the solution in an ice bath, and after stirring themixture in an ice bath for 10 minutes, 3.43 mL (45.2 mmol) ofchloro(methoxy)methane was gradually added dropwise to the mixture andthe resulting mixture was stirred in an ice bath for 1 hour. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layer was successively washed with water and brine,and dried over anhydrous magnesium sulfate. The solvent was removed, andthe obtained residue was purified by silica gel column chromatography(Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 6.54 g (39.4mmol, Yield: 95.9%) of 2-(methoxymethoxy)benzaldehyde.

(2) 1-(Methoxymethoxy)-2-vinylbenzene

Under nitrogen atmosphere, 877 mg (21.9 mmol) of 60% sodium hydridewashed with hexane was suspended in dry dimethylsulfoxide (10 mL), thesuspension was heated at 85° C. for 30 minutes with stirring, cooled toroom temperature, and then, in an ice bath, a dry dimethylsulfoxide (20mL) solution containing 7.83 g (21.9 mmol) ofmethyl(triphenyl)phosphonium bromide was gradually added dropwisethereto. After stirring at room temperature for 15 minutes, a drydimethylsulfoxide (9 mL) solution containing 3.02 g (18.2 mmol) of2-(methoxymethoxy)benzaldehyde obtained in (1) was added dropwisethereto, and the mixture was stirred at room temperature for 15 minutes.The reaction mixture was poured into water, and extracted with diethylether. The organic layer was successively washed with water and brine,and dried over anhydrous magnesium sulfate. The solvent was removed, andthe obtained residue was purified by silica gel column chromatography(Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 2.54 g (15.5mmol, Yield: 85.2%) of 1-(methoxymethoxy)-2-vinylbenzene.

(3) 1-(2-Bromo-1-fluoroethyl)-2-(methoxymethoxy)benzene

To a methylene chloride (10 mL) solution containing 1.47 g (9.13 mmol)of N,N,N-triethylamine hydrotrifluoric acid (MEC-82) was added dropwisea methylene chloride (5 mL) solution containing 1.00 g (6.09 mmol) of1-(methoxymethoxy)-2-vinylbenzene obtained in (2), and 1.19 g (6.70mmol) of N-bromosuccinimide was added thereto in an ice bath. Themixture was stirred in an ice bath as such for 2 hours, it was warmed toroom temperature and stirred for further 30 minutes. The reactionmixture was poured into a saturated aqueous sodium hydrogen carbonatesolution and extracted with methylene chloride. The organic layer wassuccessively washed with diluted hydrochloric acid, water and brine, anddried over anhydrous magnesium sulfate. The solvent was distilled offand the obtained residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05717, 4 plates were used,developed by ethyl acetate:hexane=4:1), and then, purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 4 plates were used, developed by ethyl acetate:hexane=10:1) toobtain 1.24 g of a crude product of1-(2-bromo-1-fluoroethyl)-2-(methoxymethoxy)benzene.

(4) 1-(1-Fluorovinyl)-2-(methoxymethoxy)benzene

In dry dimethylsulfoxide (10 mL) was added 736.2 mg (11.15 mmol) of 85%potassium hydroxide, the mixture was stirred at room temperature for 1hour and 30 minutes, a dry dimethylsulfoxide (6 mL) solution containing978.2 mg of a crude purified product of1-(2-bromo-1-fluoroethyl)-2-(methoxymethoxy)benzene obtained in (3) wasadded dropwise to the mixture, and the resulting mixture was stirred for2 hours and then stirred at 60° C. for 2 hours. The reaction mixture waspoured into water and extracted with hexane. The organic layer wassuccessively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was removed to obtain 632.7 mg of a crudeproduct of 1-(1-fluorovinyl)-2-(methoxymethoxy)benzene.

(5) 1-(1-Fluorocyclopropyl)-2-(methoxymethoxy)benzene

Under nitrogen atmosphere, dry diethyl ether (5 mL) was charged in a dryflask, 1.97 mL (1.97 mmol) of diethylzinc (1M hexane solution) was addeddropwise thereto, and then, a dry diethyl ether (3 mL) solutioncontaining 143.6 mg of a crude product of1-(1-fluorovinyl)-2-(methoxymethoxy)benzene obtained in (4) was addeddropwise thereto. After stirring at room temperature for 10 minutes,0.19 mL (2.3 mmol) of diiodomethane was added dropwise to the mixtureand the resulting mixture was refluxed for 4 hours and 30 minutes. Thereaction mixture was poured into a saturated aqueous ammonium chloridesolution, then, a saturated aqueous sodium hydrogen carbonate solutionwas added and the mixture was stirred for a while, and extracted withdiethyl ether. The organic layer was successively washed with water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the obtained residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 3 plateswere used, developed by ethyl acetate:hexane=4:1) to obtain 80.5 mg of acrude product of 1-(1-fluorocyclopropyl)-2-(methoxymethoxy)benzene.

(6) 2-(1-Fluorocyclopropyl)phenol

Conc. hydrochloric acid (0.3 mL) was added dropwise to a methanol (6 mL)solution containing 43.8 mg of a crude product of1-(1-fluorocyclopropyl)-2-(methoxymethoxy)benzene obtained in (5), andthe mixture was stirred at 60° C. for 3 hours. The reaction mixture waspoured into water, and extracted with ethyl acetate. The organic layerwas successively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was removed to obtain 42.8 mg of a crudeproduct of 2-(1-fluorocyclopropyl)phenol.

(7) 6-Chloro-3-[2-(1-fluorocyclopropyl)phenoxy]pyridazine 1-oxide (StepB-2)

In a mixed solvent of 1,4-dioxane(3 mL) and dimethylsulfoxide (3 mL) wasdissolved 42.8 mg of a crude product of 2-(1-fluorocyclopropyl)phenolobtained in (6), 34.7 mg (0.310 mmol) of potassium tert-butoxide wasadded to the solution, and then, 46.4 mg.(0.281 mmol) of3,6-dichloropyridazine 1-oxide was added to the mixture and theresulting mixture was stirred at room temperature overnight. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layer was successively washed with water and brine,and dried over anhydrous magnesium sulfate. The solvent was distilledoff and the obtained residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05744, 2 plates were used,developed by ethyl acetate:hexane=2:1) to obtain 28.0 mg (0.0996 mmol)of 6-chloro-3-[2-(1-fluorocyclopropyl)phenoxy]pyridazine 1-oxide.

(8) 4,6-Dichloro-3-[2-(1-fluorocyclopropyl)phenoxy]-pyridazine (StepB-3)

In phosphorus oxychloride (1 mL) was dissolved 28.0 mg (0.0996 mmol) of6-chloro-3-[2-(1-fluorocyclopropyl)phenoxy]pyridazine 1-oxide obtainedin (7), and the solution was stirred at room temperature overnight. Tothe mixture were added water and methylene chloride, and after stirringfor 30 minutes, the mixture was extracted with methylene chloride. Theorganic layer was successively washed with water and brine, and driedover anhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 2 plates were used, developed byethyl acetate:hexane=2:1) to obtain 5.1 mg (0.017 mmol, Yield: 17%) of4,6-dichloro-3-[2-(1-fluorocyclopropyl)phenoxy]pyridazine.

(9) 6-Chloro-3-[2-(1-fluorocyclopropyl)phenoxy]-4-pyridazinol (CompoundNo. 140, Step B-4)

In a mixed solvent of 1,4-dioxane (2 mL) and dimethylsulfoxide (2 mL)was dissolved 5.1 mg (0.017 mmol) of4,6-dichloro-3-[2-(1-fluorocyclopropyl)phenoxy]pyridazine obtained in(8), and to the solution was added 0.1 mL of 2 mol/L of aqueous sodiumhydroxide solution, and the resulting mixture was stirred at roomtemperature overnight. The reaction mixture was poured into water,diluted hydrochloric acid was added to the mixture to adjust pH 2, andextracted with ethyl acetate. The organic layer was successively washedwith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 1 plate was used, developed by ethyl acetate) to obtain 4.0 mg(0.014 mmol, Yield: 82%) of6-chloro-3-[2-(1-fluorocyclopropyl)phenoxy]-4-pyridazinol (Compound No.140).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.57-7.52 (1H, m), 7.39-7.31 (1H, m),7.22-7.13 (1H, m), 7.00 (1H, d, J=8.1 Hz), 6.48 (1H, s), 1.32-1.22 (2H,m), 1.16-1.08 (2H, m). Melting point (° C.): 152-157.

EXAMPLE 86-Chloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}-4-pyridazinol(Compound No. 207) (1) 1-Methoxy-2-vinylbenzene

Under nitrogen atmosphere, in dry dimethylsulfoxide (15 mL) wassuspended 1.92 g (48.0 mmol) of 60% sodium hydride washed with hexane,after stirring the suspension at 85° C. for 30 minutes, it was cooled toroom temperature and then, in an ice bath, a dry dimethylsulfoxide (35mL) solution containing 17.2 g (48.2 mmol) ofmethyl(triphenyl)phosphonium bromide was gradually added dropwisethereto. After stirring at room temperature for 20 minutes, 4.83 mL(40.1 mmol) of commercially available 2-methoxybenzaldehyde was addeddropwise thereto, and the resulting mixture was stirred at roomtemperature for 1 hour and then at 65° C. for 3 hours. The reactionmixture was poured into ice water, and extracted with ethyl acetate. Theorganic layer was successively washed with water and brine, and driedover anhydrous magnesium sulfate. The solvent was removed, and theobtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 3.29 g (24.5 mmol,Yield: 61.1%) of 1-methoxy-2-vinylbenzene.

(2) 1-(2-Bromo-1-fluoroethyl)-2-methoxybenzene

To a methylene chloride (20 mL) solution containing 3.60 g (22.4 mmol)of N,N,N-triethylamine hydrotrifluoric acid (MEC-82) was added dropwisea methylene chloride (6 mL) solution containing 2.01 g (15.0 mmol) of1-methoxy-2-vinylbenzene obtained in (1), and 2.92 g (16.4 mmol) ofN-bromosuccinimide was added in an ice bath. Stirring was continued inan ice bath for 25 minutes, and the mixture was warmed to roomtemperature and further stirred for 1 hour and 30 minutes. The reactionmixture was poured into a saturated aqueous sodium hydrogen carbonatesolution and extracted with methylene chloride. The organic layer wassuccessively washed with diluted hydrochloric acid, water and brine, anddried over anhydrous magnesium sulfate. The solvent was removed, and theobtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 1.39 g of a crudeproduct of 1-(2-bromo-1-fluoroethyl)-2-methoxybenzene.

(3) 1-(1-Fluorovinyl)-2-methoxybenzene

To dry dimethylsulfoxide (10 mL) was added 1.28 g (19.4 mmol) of 85%potassium hydroxide, the mixture was stirred at room temperature for 30minutes, and then, a dry dimethylsulfoxide (10 mL) solution containing1.50 g of a crude product of 1-(2-bromo-1-fluoroethyl)-2-methoxybenzeneobtained in (2) was added dropwise thereto, and the mixture was stirredovernight. The reaction mixture was poured into water and extracted withhexane. The organic layer was successively washed with water and brine,and dried over anhydrous magnesium sulfate. The solvent was removed, andthe obtained residue was purified by silica gel column chromatography(Wako gel C-100, hexane-ethyl acetate, gradient) to obtain 1.21 g of acrude product of 1-(1-fluorovinyl)-2-methoxybenzene.

(4) 1-(1-Fluorocyclopropyl)-2-methoxybenzene

Under nitrogen atmosphere, dry diethyl ether (8 mL) was charged in a dryflask, 19.88 mL (19.88 mmol) of diethylzinc (1 mol/L hexane solution)was added dropwise thereto, and a dry diethyl ether (8 mL) solutioncontaining 1.21 g of a crude product of1-(1-fluorovinyl)-2-methoxybenzene obtained in (3) was added dropwisethereto. After stirring at room temperature for 10 minutes, 1.92 mL(23.86 mmol) of diiodomethane was added dropwise thereto, and themixture was refluxed for 6 hours. After allowing to stand at roomtemperature overnight, the reaction mixture was poured into a saturatedaqueous ammonium chloride solution, and then, a saturated aqueous sodiumhydrogen carbonate solution was added thereto and the mixture wasstirred for a while, and extracted with diethyl ether. The organic layerwas successively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was removed, and the obtained residue waspurified by silica gel column chromatography (Wako gel C-100,hexane-ethyl acetate, gradient) to obtain 1.06 g of a crude product of1-(1-fluorocyclopropyl)-2-methoxybenzene.

(5) 2-[1-(ethylsulfanyl)cyclopropyl]phenol

Under nitrogen atmosphere, in dry N,N-dimethylformamide (8 mL) wassuspended 765.3 mg (19.1 mmol) of 60% sodium hydride, and to thesuspension was gradually added dropwise 1.46 mL (19.8 mmol) ofethanethiol and after stirring for 15 minutes, a dryN,N-dimethylformamide (5 mL) solution containing 1.06 g of a crudeproduct of 1-(1-fluorocyclopropyl)-2-methoxybenzene obtained in (4) wasadded dropwise thereto and the resulting mixture was stirred at 160° C.for 5 hours. After cooling by allowing to stand, 1 mol/L of aqueouspotassium hydroxide solution and diethyl ether were added to thereaction mixture. The aqueous layer was separated, and washed withdiethyl ether. To the mixture was added diluted hydrochloric acid toadjust pH to 2, and extracted with diethyl ether. The organic layer wassuccessively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was removed, and the obtained residue waspurified by silica gel column chromatography (Wako gel C-100,hexaneethyl acetate, gradient) to obtain 0.26 g of a crude product of2-[1-(ethylsulfanyl)cyclopropyl]phenol.

(6) 6-Chloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}-pyridazine1-oxide (Step B-2)

In a mixed solvent of 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL)was dissolved 0.26 g of a crude product of2-[1-(ethylsulfanyl)cyclopropyl]phenol obtained in (5), 265.5 mg (2.37mmol) of potassium tert-butoxide was added to the solution, and then,390.3 mg (2.37 mmol) of 3,6-dichloropyridazine 1-oxide was added to thesame, and the resulting mixture was stirred at room temperatureovernight. The reaction mixture was poured into water, and extractedwith ethyl acetate. The organic layer was successively washed with waterand brine, and dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the obtained residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 3 plateswere used, developed by ethyl acetate:hexane=2:1) to obtain 138.4 mg(0.428 mmol) of6-chloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}pyridazine 1-oxide.

(7) 4,6-Dichloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]-phenoxy}pyridazine(Step B-3)

In phosphorus oxychloride (1 mL) was dissolved 138.4 mg (0.428 mmol) of6-chloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}pyridazine 1-oxideobtained in (6), and the solution was stirred at room temperatureovernight. To the reaction mixture were added water and methylenechloride, and the mixture was stirred for 30 minutes and extracted withmethylene chloride. The organic layer was successsively washed withwater and brine, and dried over anhydrous magnesium sulfate. The solventwas distilled off and the obtained residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 2 plateswere used, developed by ethyl acetate:hexane=4:1) to obtain 94.4 mg(0.277 mmol, Yield: 64.7%) of4,6-dichloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}pyridazine.

(8) 6-Chloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}-4-pyridazinol(Compound No. 207, Step B-4)

In a mixed solvent of 1,4-dioxane (1 mL) and dimethylsulfoxide (1 mL)was dissolved 94.4 mg (0.277 mmol) of4,6-dichloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}pyridazineobtained in (7), 0.69 mL (1.38 mmol) of 2 mol/L aqueous sodium hydroxidesolution was added to the solution, and the mixture was stirred at roomtemperature overnight. To the reaction mixture were added water andethyl acetate, the aqueous layer was separated and washed with ethylacetate. Diluted hydrochloric acid was added thereto to adjust pH to 2,and the mixture was extracted with ethyl acetate. The organic layer wassuccessively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05744, 2 plates were used, developed by ethyl acetate)to obtain 47.5 mg (0.147 mmol, Yield: 53.1%) of6-chloro-3-{2-[1-(ethylsulfanyl)cyclopropyl]phenoxy}-4-pyridazinol(Compound No. 207).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.45-7.07 (4H, m), 6.69 (1H, s), 2.46(2H, q, J=7.3 Hz), 1.28-1.02 (9H, m). Melting point (° C.): 88.

EXAMPLE 9 6-Chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]-4-pyridazinol(Compound No. 265) (1)1-(2,2-dichlorocyclopropyl)-2-(methoxymethoxy)benzene

In chloroform (12 mL) was dissolved 305 mg (1.86 mmol) of1-(methoxymethoxy)-2-vinylbenzene obtained in Example 7(2), 5 mL (63mmol) of 50% aqueous sodium hydroxide solution was added dropwise to thesolution, and then, 54.1 mg (0.237 mmol) of benzyl(triethyl)ammoniumchloride was added to the same and the resulting mixture was stirred atroom temperature overnight. The reaction mixture was poured into water,and extracted with chloroform. The organic layer was successively washedwith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by ethyl acetate:hexane=1:2) toobtain 387 mg (1.57 mmol, Yield: 84.4%) of1-(2,2-dichlorocyclopropyl)-2-(methoxymethoxy)benzene.

(2) 2-(2,2-Dichlorocyclopropyl)phenol

In methanol (5 mL) was dissolved 203 mg (0.822 mmol) of1-(2,2-dichlorocyclopropyl)-2-(methoxymethoxy)benzene obtained in (1),0.1 mL of conc. hydrochloric acid was added to the solution, and theresulting mixture was stirred at 60° C. for 2 hours. After confirmingdisappearance of the starting materials by thin layer chromatography,the reaction mixture was poured into water, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, and dried over anhydrous magnesium sulfate. The solventwas removed to obtain 194 mg of a crude product of2-(2,2-dichlorocyclopropyl)phenol.

(3) 6-Chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]-pyridazine 1-oxide(Step B-2)

In a mixed solvent of 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL)was mixed 194 mg of a crude product of 2-(2,2-dichlorocyclopropyl)phenolobtained in (2), 118 mg (1.05 mmol) of potassium tert-butoxide was addedto the mixture in an ice bath, and the resulting mixture was stirred for10 minutes. To the mixture was added 157 mg (0.952 mmol) of3,6-dichloropyridazine 1-oxide, and the mixture was stirred at roomtemperature overnight. The reaction mixture was poured into ice-coldwater, and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05744, 3 plates were used, developed by ethylacetate:hexane=1:2) to obtain 268 mg of a crude product of6-chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]pyridazine 1-oxide.

(4) 4,6-Dichloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]-pyridazine (StepB-3)

268 mg of a crude product of6-chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]pyridazine 1-oxideobtained in (3) and 3 mL of phosphorus oxychloride were mixed, and themixture was stirred at room temperature overnight. To the reactionmixture were added water and dichloromethane, and the resulting mixturewas stirred for 30 minutes. The mixture was separated, and the organiclayer was successively washed with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05744, 3 plates were used, developed by ethylacetate:hexane=1:2) to obtain 162 mg (0.463 mmol, Yield with 3 stepsfrom 1-(2,2-dichlorocyclopropyl)-2-(methoxymethoxy)benzene: 56.3%) of4,6-dichloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]pyridazine.

(5) 6-Chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]-4-pyridazinol(Compound No. 265, Step B-4)

162 mg (0.463 mmol) of4,6-dichloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]pyridazine obtainedin (4), 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL) were mixed, tothe mixture was added 1.15 mL (2.30 mmol) of 2 mol/L aqueous sodiumhydroxide solution, and the mixture was stirred at room temperatureovernight. The reaction mixture was poured into water, and made acidicwith diluted hydrochloric acid. The mixture was extracted withdichloromethane. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 3 plateswere used, developed by ethyl acetate) to obtain 50.0 mg (0.151 mmol,Yield: 32.6%) of6-chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]-4-pyridazinol (CompoundNo. 265).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.55-7.15 (4H, m), 6.69 (1H, s), 2.90(1H, dd, J=10.6, 8.8 Hz), 2.07-1.89 (2H, m). Melting point (° C.):158-163.

EXAMPLE 10 6-Chloro-3-(2-hydroxyphenoxy)-4-pyridazinol (Compound No.384) (1) 3-Chloro[1,4]benzodioxino[2,3-c]pyridazine(Step O-1)

In 1,4-dioxane (30 mL) was suspended 3.49 g (80.0 mmol) of 55% sodiumhydride, and to the suspension were added a 1,4-dioxane (30 mL) solutioncontaining 4.40 g (40 mmol) of pyrocatechol, then a 1,4-dioxane (30 mL)solution containing 7.30 g (39.9 mmol) of 3,4,6-trichloropyridazine{described in The Journal of Organic Chemistry, 1963, vol. 28, pp. 218to 221}, and the mixture was refluxed for 2 hours. The reaction mixturewas poured into ice-cold water, and extracted with ethyl acetate. Theorganic layers were combined, washed successively with 1 mol/L sodiumhydroxide and water, and dried over anhydrous magnesium sulfate. Thesolvent was removed, and the residue was recrystallized from methylisobutyl ketone to obtain 6.15 g (27.8 mmol, Yield: 69.7%) of3-chloro[1,4]benzodioxino[2,3-c]pyridazine.

(2) 6-Chloro-3-(2-hydroxyphenoxy)-4-pyridazinol (Compound No. 384, StepO-2)

A mixture comprising 5.52 g (25.0 mmol) of3-chloro[1,4]benzodioxino[2,3-c]pyridazine obtained in (1), 1.30 g (31.2mmol) of 96% sodium hydroxide, dimethylsulfoxide (55 mL) and water (15mL) was stirred at 90° C. for 1 hour. The reaction mixture was pouredinto ice-cold water, made acidic with hydrochloric acid, and extractedwith ethyl acetate. The solvent was removed, and the residue was washedwith isopropyl ether to obtain 4.90 g (20.5 mmol, Yield: 82.0%) of6-chloro-3-(2-hydroxyphenoxy)-4-pyridazinol (Compound No. 384).

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.25-6.40 (5H, m). Melting point (° C.):216-219.

EXAMPLE 11 6-Chloro-3-[2-(methylsulfinyl)phenoxy]-4-pyridazinol(Compound No. 404) (1) 6-Chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine1-oxide (Step B-2)

In a mixed solvent of 1,4-dioxane (5 mL) and dimethylsulfoxide (5 mL)was dissolved 454 mg (3.24 mmol) of 2-(methylsulfanyl)phenol, to thesolution was added 519 mg (4.63 mmol) of potassium tert-butoxide and themixture was stirred for 35 minutes. To the mixture was added 424 mg(2.57 mmol) of 3,6-dichloropyridazine 1-oxide and the resulting mixturewas stirred for 3 hours. The reaction mixture was poured into water andextracted with ethyl acetate. The organic layers were combined, washedwith brine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the obtained residue was purified by silica gelchromatography (Wakogel C-100, eluted with hexane:ethyl acetate=3:1) toobtain 391 mg (1.46 mmol, Yield: 56.8%) of6-chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine 1-oxide.

(2) 4,6-Dichloro-3-[2-(methylsulfanyl)phenoxy]pyridazine (Step B-3)

288 mg (1.07 mmol) of 6-chloro-3-[2-(methylsulfanyl)-phenoxy]pyridazine1-oxide obtained in (1) and 1.00 mL (10.8 mmol) of phosphorusoxychloride were mixed, and the mixture was stirred overnight. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layer was washed successively with a saturatedaqueous sodium hydrogen carbonate solution and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theresidue was purified by preparative thin-layer chromatography (availablefrom Merck Co., 1.05744, developed by hexane/ethyl acetate=3/1) toobtain 118 mg (0.411 mmol, Yield: 38.4%) of4,6-dichloro-3-[2-(methylsulfanyl)phenoxy]pyridazine.

(3) 4,6-Dichloro-3-[2-(methylsulfinyl)phenoxy]pyridazine

In 1,2-dichloroethane (4 mL) was dissolved 118 mg (0.411 mmol) of4,6-dichloro-3-[2-(methylsulfanyl)phenoxy]pyridazine obtained in (2),96.3 mg (purity 80%, 0.446 mmol) of m-chloroperbenzoic acid was added tothe solution and the resulting mixture was stirred at room temperaturefor 5 hours. The reaction mixture was poured into 10% aqueous sodiumsulfite solution, extracted with ethyl acetate, then washed with brine,and dried over anhydrous magnesium sulfate. The solvent was distilledoff and the obtained residue was purified by preparative thin-layerchromatography (available from Merck Co., 1.05744, developed byhexane:ethyl acetate=1:1, then, 3:1, and then, 1:1) to obtain 21.1 mg(0.0696 mmol, Yield: 16.9%) of4,6-dichloro-3-[2-(methylsulfinyl)phenoxy]pyridazine.

(4) 6-Chloro-3-[2-(methylsulfinyl)phenoxy]-4-pyridazinol (Compound No.404, Step B-4)

In 1,4-dioxane (0.5 mL) was dissolved 21.1 mg (0.0696 mmol) of4,6-dichloro-3-[2-(methylsulfinyl)phenoxy]pyridazine obtained in (3),0.12 mL (0.36 mmol) of 3 mol/L aqueous sodium hydroxide solution wasadded to the solution, and the resulting mixture was stirred for 45minutes. To the mixture was added dimethylsulfoxide (0.5 mL), and afterstirring for 3 hours, the reaction mixture was poured into 10%hydrochloric acid and extracted with ethyl acetate. The organic layerwas successively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom Merck Co., 1.05744, chloroform:methanol=10:1) to obtain 2.1 mg(0.0074 mmol, Yield: 11%) of6-chloro-3-[2-(methylsulfinyl)phenoxy]-4-pyridazinol (Compound No. 404).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.90-7.84 (1H, m), 7.60-7.42 (2H, m),7.14 (1H, dd, J=9.2, 1.1 Hz), 6.62 (1H, s), 2.92 (3H, s). Appearance:amorphous.

EXAMPLE 12 6-Chloro-3-[2-(methylsulfonyl)phenoxy]-4-pyridazinol(Compound No. 406) (1) 6-Chloro-3-[2-(methylsulfonyl)phenoxy]pyridazine1-oxide

In 1,2-dichloroethane (5 mL) was dissolved 208 mg (0.774 mmol) of6-chloro-3-[2-(methylsulfanyl)phenoxy]pyridazine 1-oxide obtained inExample 11 (1), 829 mg (3.84 mmol) of 80% m-chloroperbenzoic acid wasadded to the solution and the resulting mixture was stirred at roomtemperature for 4 hours. The reaction mixture was poured into 10%aqueous sodium sulfite solution, and extracted with ethyl acetate. Theorganic layers were combined, washed with brine and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom Merck Co., 1.05744, developed by hexane:ethyl acetate=1:1) toobtain 132 mg (0.439 mmol, Yield: 56.7%) of6-chloro-3-[2-(methylsulfonyl)phenoxy]pyridazine 1-oxide.

(2) 4,6-Dichloro-3-[2-(methylsulfonyl)phenoxy]pyridazine (Step B-3)

111 mg (0.369 mmol) of 6-chloro-3-[2-(methylsulfonyl)phenoxy]pyridazine1-oxide obtained in (1) and 1.00 mL (10.8 mmol) of phosphorusoxychloride were mixed, and the mixture was stirred overnight. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layer was successively washed with a saturatedsodium hydrogen carbonate and brine, and dried over anhydrous magnesiumsulfate. The solvent was distilled off and the residue was purified bypreparative thin-layer chromatography (available from Merck Co.,1.05744, developed by hexane:ethyl acetate=1:1) to obtain 70.8 mg (0.222mmol, Yield: 60.2%) of4,6-dichloro-3-[2-(methylsulfonyl)phenoxy]pyridazine.

(3) 6-Chloro-3-[2-(methylsulfonyl)phenoxy]-4-pyridazinol (Compound No.406, Step B-4)

In 1,4-dioxane (2.0 mL) was dissolved 70.8 mg (0.222 mmol) of4,6-dichloro-3-[2-(methylsulfonyl)phenoxy]pyridazine obtained in (2),0.45 mL (1.4 mmol) of 3 mol/L aqueous sodium hydroxide solution wasadded to the solution, and the resulting mixture was stirred for 30minutes. To the mixture was added dimethylsulfoxide (2.0 mL), themixture was stirred overnight, poured into water and washed with a mixedsolvent of hexane-ethyl acetate. To the aqueous layer was added 10%hydrochloric acid to make it acidic, and the mixture was extracted withethyl acetate. The organic layer was successively washed with water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the obtained residue was purified by preparativethin-layer chromatography (available from Merck Co., 1.05744, developedby chloroform:methanol=10:1) to obtain 18.0 mg (0.0599 mmol, Yield:27.0%) of 6-chloro-3-[2-(methylsulfonyl)phenoxy]-4-pyridazinol (CompoundNo. 406).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.00 (1H, dd, J=7.7, 1.8 Hz), 7.71 (1H,ddd, J=7.7, 7.7, 1.8 Hz), 7.43 (1H, ddd, J=7.7, 7.7, 1.1 Hz), 7.32 (1H,br.d, J=7.7 Hz), 6.62 (1H, s), 3.36 (3H, s). Appearance: amorphous.

EXAMPLE 13 6-Chloro-3-(2-cyclopropyl-3-methoxyphenoxy)-4-pyridazinol(Compound No. 478) (1)6-Chloro-3-(2-cyclopropyl-3-methoxyphenoxy)-4-methoxy-pyridazine (StepD-1)

In a mixed solvent of 1,4-dioxane (2.5 mL) and dimethylsulfoxide (2.5mL) was dissolved 190 mg (1.16 mmol) of 2-cyclopropyl-3-methoxyphenol,146 mg (1.30 mmol) of potassium tert-butoxide was added to the solutionand the resulting mixture was stirred for 10 minutes. To the mixture wasadded 170 mg (0.950 mmol) of 3,6-dichloro-4-methoxypyridazine and theresulting mixture was stirred overnight. The reaction mixture was pouredinto ice water and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel chromatography (Wakogel C-100,hexane-ethyl acetate, gradient) to obtain 90.1 mg (0.293 mmol, Yield:30.8%) of6-chloro-3-(2-cyclopropyl-3-methoxyphenoxy)-4-methoxypyridazine and 114mg (0.371 mmol, Yield: 39.1%) of3-chloro-6-(2-cyclopropyl-3-methoxyphenoxy)-4-methoxypyridazine.

(2) 6-Chloro-3-(2-cyclopropyl-3-methoxyphenoxy)-4-pyridazinol (CompoundNo. 478, Step D-2)

In dry N,N-dimethylformamide (DMF, 2 mL) was suspended 24 mg (0.60 mmol)of 60% sodium hydride, 0.05 mL (0.7 mmol) of ethanethiol was addeddropwise to the suspension in an ice bath and the resulting mixture wasstirred at room temperature for 10 minutes. To the mixture was added adry N,N-dimethylformamide (DMF, 1.5 mL) solution containing 60.0 mg(0.195 mmol,) of6-chloro-3-(2-cyclopropyl-3-methoxyphenoxy)-4-methoxypyridazine obtainedin (1), and the resulting mixture was refluxed for 2 hours. The reactionmixture was cooled, and poured into ice-cold 1 mol/L aqueous sodiumhydroxide solution, and washed with ethyl acetate. Ice-cold conc.hydrochloric acid was added to the aqueous layer to adjust pH to 4, andthe mixture was extracted with ethyl acetate. The ethyl acetate extractswere combined, washed successively with water and brine, and dried oversodium sulfate. The solvent was distilled off and the obtained residuewas purified by preparative thin-layer chromatography (available fromMerck Co., 1.05744, 3 plates were used, developed by hexane:ethylacetate=1:1) to obtain 15.2 mg (0.0519 mmol, Yield: 26.6%) of6-chloro-3-(2-cyclopropyl-3-methoxyphenoxy)-4-pyridazinol (Compound No.478).

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.19 (1H, dd, J=8.1, 8.4 Hz), 6.76 (1H,d, J=8.1 Hz), 6.69 (1H, d, J=8.4 Hz), 6.60 (1H, s), 3.85 (3H, s),1.55-1.35 (1H, m), 0.85-0.60 (4H, m). Melting point (° C.): 184-185.

EXAMPLE 143-(1,1a,6,6a-Tetrahydrocyclopropa[a]inden-2-yloxy)-6-chloro-4-pyridazinol(Compound No. 515) (1) 7-hydroxy-1-indanone

37.0 g (278 mmol) of aluminum chloride was mixed with 3.70 g (61.3 mmol)of sodium chloride, the mixture was dissolved at 150° C. under heating,6.40 g (43.2 mmol) of commercially available2,3-dihydro-4H-chromen-4-one dissolved by heating (50° C.) was added tothe mixture and the resulting mixture was stirred at 200° C. for 20minutes. The reaction mixture (gum state) was cooled, and added toice-cold hydrochloric acid (100 ml of conc. hydrochloric acid and icewere combined to make them 200 ml) little by little and stirred for 30minutes. Methylene chloride was added to the mixture and the mixture wasseparated. The aqueous layer was filtered, and the filtrate wasextracted with methylene chloride. The organic layers were combined,washed successively with water and brine, and dried over sodium sulfate.The solvent was removed, and the obtained residue was purified by silicagel chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) toobtain 4.82 g (32.6 mmol, Yield: 75.2%) of 7-hydroxy-1-indanone.

(2) 7-(Methoxymethoxy)-1-indanone

In N,N-dimethylformamide (DMF, 33 mL) was dissolved 1.00 g (6.76 mmol)of 7-hydroxy-1-indanone obtained in (1), the solution was cooled in anice bath, and 0.330 g (8.25 mmol) of 60% sodium hydride was added bydividing into four times and the resulting mixture was stirred for 30minutes. To the mixture was added dropwise 0.80 mL (11 mmol) ofchloromethoxymethane, and the mixture was stirred at room temperaturefor 2 hours. The reaction mixture was poured into an ice-cold saturatedaqueous ammonium chloride solution (100 mL) and extracted with ethylacetate. The organic layer was washed successively with water and andbrine, dried over sodium sulfate. The solvent was removed, and theobtained residue was purified by silica gel chromatography (WakogelC-100, hexane-ethyl acetate, gradient) to obtain 1.04 g (5.42 mmol,Yield: 80.2%) of 7-(methoxymethoxy)-1-indanone.

(3) 7-(Methoxymethoxy)-1-indanol

In methanol(20 mL) was dissolved 1.04 g (5.42 mmol) of7-methoxymethoxy-1-indanone obtained in (2), the solution was cooled inan ice bath, and 164 mg (4.34 mmol) of sodium borohydride was added tothe solution and the resulting mixture was stirred at room temperaturefor 4 hours. The reaction mixture was poured into ice water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over sodium sulfate. Thesolvent was removed, and the obtained residue was purified by silica gelchromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain1.05 g (5.42 mmol, Yield: 100%) of 7-(methoxymethoxy)-1-indanol.

(4) Mixture of 4-(methoxymethoxy)-1H-indene and7-(methoxymethoxy)-1H-indene

In methylene chloride (3 mL) was dissolved 500 mg (2.58 mmol) of7-(methoxymethoxy)-1-indanol obtained in (3), the solution was cooled inan ice bath, and 0.50 mL (3.7 mmol) of triethylamine and 0.25 mL (3.3mmol) of methanesulfonyl chloride were added to the solution and theresulting mixture was stirred for 2 hours. To the mixture was added 0.80mL (5.7 mmol) of triethylamine and the mixture was stirred for 1 hour,then the mixture was poured into water and extracted with methylenechloride. The organic layer was successively washed with water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the resulting residue was dissolved in pyridine (3 mL), andthe mixture was refluxed for 4 hours. After allowing to stand at roomtemperature overnight, the reaction mixture was poured into water andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel chromatography (Wakogel C-100, hexane-ethyl acetate,gradient) to obtain 280 mg (1.59 mmol, Yield: 61.6%) of a mixture of4-(methoxymethoxy)-1H-indene and 7-(methoxymethoxy)-1H-indene.

(5) Mixture of(2-(methoxymethoxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene and5-(methoxymethoxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene

In 30 mL of eggplant type flask was charged dry diethyl ether (5 mL)under nitrogen atmosphere, and cooled in an ice bath. To the solutionwere successively added dropwise 6.3 mL (6.3 mmol) of diethylzinc (1.0mol/L hexane solution), and 0.70 mL (8.5 mmol) of diiodomethane, and themixture was stirred for 10 minutes. To the mixture was gradually addeddropwise an ether solution (9 mL) containing 250 mg (1.42 mmol) of amixture comprising 4-(methoxymethoxy)-1H-indene and7-(methoxymethoxy)-1H-indene obtained in (4). The resulting mixture wasrefluxed for 4 hours. The reaction mixture was cooled, and poured into asaturated aqueous ammonium chloride solution. To the mixture was addedthe same volume of a saturated aqueous sodium hydrogen carbonatesolution, and then, extracted with ether. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel chromatography (Wakogel C-100,hexane-ethyl acetate, gradient) to obtain 150 mg (0.789 mmol, Yield:55.6%) of a mixture of2-(methoxymethoxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene and5-(methoxymethoxy)-1,1a,6,6a-tetrahydrocyclopropa[a]-indene.

(6) Mixture of 1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-ol and1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-ol

In methanol (6 mL) was dissolved 150 mg (0.789 mmol) of a mixture of2-(methoxymethoxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene and5-(methoxymethoxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene obtained in(5), two drops of conc. hydrochloric acid were added to the solution andthe resulting mixture was stirred at room temperature for 1 hour andthen at 60° C. for 20 minutes. The reaction mixture was cooled, pouredinto water and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous sodium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom Merck Co., 1.05744, developed by hexane:ethyl acetate=2:1) toobtain 80.0 mg (0.548 mmol, Yield: 69.5%) of a mixture of1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-ol and1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-ol.

(7) Mixture of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-yloxy)-6-chloropyridazine1-oxide and3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-yloxy)-6-chloropyridazine1-oxide (Step B-2)

In a mixed solvent of 1,4-dioxane (2 mL) and dimethylsulfoxide (2 mL)was dissolved 80.0 mg (0.548 mmol) of a mixture of1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-ol and1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-ol obtained in (6), and 85 mg(0.76 mmol) of potassium tert-butoxide was added to the solution and themixture was stirred for 10 minutes. To the mixture was added 82 mg (0.50mmol) of 3,6-dichloropyridazine 1-oxide, and the resulting mixture wasstirred at room temperature overnight. The reaction mixture was pouredinto water and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from Merck Co., 1.05744, 4 plates were used, developed byhexane:ethyl acetate=2:1) to obtain 75.0 mg (0.273 mmol, Yield: 49.8%)of a mixture of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-yloxy)-6-chloropyridazine1-oxide and3-(1,1a,6,6a-tetrahydrocyclopropa-[a]inden-5-yloxy)-6-chloropyridazine1-oxide.

(8)3-(1,1a,6,6a-Tetrahydrocyclopropa[a]inden-2-yloxy)-4,6-dichloropyridazineand3-(1,1a,6,6a-tetrahydrocyclopropa-[a]inden-5-yloxy)-4,6-dichloropyridazine(Step B-3)

75.0 mg (0.273 mmol) of a mixture of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-yloxy)-6-chloropyridazine1-oxide and3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-yloxy)-6-chloropyridazine1-oxide obtained in (7) was mixed with 0.30 mL (3.2 mmol) of phosphorusoxychloride, and the mixture was stirred overnight. The reaction mixturewas concentrated under reduced pressure to remove phosphorusoxychloride, and the residue was purified by preparative thin-layerchromatography (available from Merck Co., 1.05744, 3 plates were used,developed by hexane/ethyl acetate=9/1 four times repeatedly) to obtain21.4 mg (0.0730 mmol, Yield: 26.7%) of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-yloxy)-4,6-dichloropyridazineand 32.6 mg (0.111 mmol, Yield: 40.7%) of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-yloxy)-4,6-dichloropyridazine.

(9)3-(1,1a,6,6a-Tetrahydrocyclopropa[a]inden-2-yloxy)-6-chloro-4-pyridazinol(Compound No. 515, Step B-4)

To a dimethylsulfoxide (3 mL) solution containing 21.4 mg (0.0730 mmol)of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-yloxy)-4,6-dichloropyridazineobtained in (8) was added 0.1 mL (0.2 mmol) of 2 mol/L aqueous sodiumhydroxide solution, and the mixture was stirred at room temperature for3 hours. The reaction mixture was poured into ice-cold 1 mol/L aqueoussodium hydroxide solution, and extracted with ethyl acetate. The aqueouslayer was separated, conc. hydrochloric acid was added thereto to adjustpH to 4 in an ice bath, and the mixture was extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, dried over sodium sulfate. The solvent was distilledoff and the obtained residue was purified by preparative thin-layerchromatography (available from Merck Co., 1.05744, 1 plate was used,developed by chloroform:methanol=10:1) to obtain 10.3 mg (0.0375 mmol,Yield: 51.4%) of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-2-yloxy)-6-chloro-4-pyridazinol(Compound No. 515).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.08 (1H, t, J=7.7 Hz), 6.98 (1H, d,J=7.7 Hz), 6.84 (1H, d, J=7.7 Hz), 6.59 (1H, s), 3.20 (1H, dd, J=17.2,6.2 Hz), 2.94 (1H, d, J=17.2 Hz), 2.30-2.15 (1H, m), 1.90-1.75 (1H, m),1.05-0.90 (1H, m). Melting point (° C.): 245-247.

EXAMPLE 153-(1,1a,6,6a-Tetrahydrocyclopropa[a]inden-5-yloxy)-6-chloro-4-pyridazinol(Compound No. 516, Step B-4)

In dimethylsulfoxide (3 mL) was dissolved 32.6 mg (0.111 mmol) of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-yloxy)-4,6-dichloropyridazineobtained in Example 14(8), and 0.1 mL (0.2 mmol) of 2 mol/L aqueoussodium hydroxide solution was added to the solution and the resultingmixture was stirred at room temperature for 4 hours. The reactionmixture was poured into ice-cold 1 mol/L aqueous sodium hydroxidesolution, and washed with ethyl acetate. The aqueous layer wasseparated, conc. hydrochloric acid was added thereto to adjust pH to 4in an ice bath, and extracted with ethyl acetate. The organic layerswere combined, washed successively with water and brine, dried oversodium sulfate. The solvent was distilled off and the obtained residuewas purified by preparative thin-layer chromatography (available fromMerck Co., 1.05744, 1 plate was used, developed bychloroform:methanol=10:1) to obtain 13.4 mg (0.0487 mmol, Yield: 43.9%)of3-(1,1a,6,6a-tetrahydrocyclopropa[a]inden-5-yloxy)-6-chloro-4-pyridazinol(Compound No. 516).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.25-7.05 (2H, m), 6.83 (1H, dd, J=6.6,2.6 Hz), 6.67 (1H, s), 3.00 (1H, dd, J=17.2, 6.6 Hz), 2.78 (1H, d,J=17.2 Hz), 2.50-2.35 (1H, m), 2.00-1.80 (1H, m), 1.15-1.00 (1H, m),0.10-0.00 (1H, m). Melting point (° C.): 211-213.

EXAMPLE 16 6-Chloro-3-(2-methoxy-5-methylphenoxy)-4-pyridazinol(Compound No. 704) (1) 6-Chloro-3-(2-methoxy-5-methylphenoxy)pyridazine1-oxide (Step B-2)

In a mixed solvent of 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL)was dissolved 167.5 mg (1.21 mmol) of commercially available2-methoxy-5-methylphenol, and 142.8 mg (1.27 mmol) of potassiumtert-butoxide was added to the solution, then 202.9 mg (1.23 mmol) of3,6-dichloropyridazine 1-oxide was added to the mixture and theresulting mixture was stirred at room temperature overnight. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layer was successively washed with water and brine,and dried over anhydrous magnesium sulfate. The solvent was distilledoff and the obtained residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05744, 3 plates were used,developed by ethyl acetate:hexane=2:1) to obtain 226.5 mg (0.849 mmol,Yield: 70.2%) of 6-chloro-3-(2-methoxy-5-methylphenoxy)pyridazine1-oxide.

(2) 4,6-Dichloro-3-(2-methoxy-5-methylphenoxy)pyridazine (Step B-3)

In phosphorus oxychloride (1 mL) was dissolved 226.5 mg (0.849 mmol) of6-chloro-3-(2-methoxy-5-methylphenoxy)-pyridazine 1-oxide obtained in(1), and the solution was stirred at room temperature overnight. To thereaction mixture were added water and methylene chloride, and afterstirring for 30 minutes, it was extracted with methylene chloride. Theorganic layer was successively washed with water and brine, and driedover anhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 3 plates were used, developed byethyl acetate:hexane=2:1) to obtain 205.3 mg (0.720 mmol, Yield: 84.8%)of 4,6-dichloro-3-(2-methoxy-5-methylphenoxy)pyridazine.

(3) 6-Chloro-3-(2-methoxy-5-methylphenoxy)-4-pyridazinol (Compound No.704, Step B-4)

In a mixed solvent of 1,4-dioxane (5 mL) and dimethylsulfoxide (5 mL)was dissolved 205.3 mg (0.720 mmol) of4,6-dichloro-3-(2-methoxy-5-methylphenoxy)pyridazine obtained in (2),and 1.8 mL (3.6 mmol) of 2 mol/L aqueous sodium hydroxide solution wasadded to the solution, and the resulting mixture was stirred at roomtemperature overnight. Water was added to the reaction mixture, dilutedhydrochloric acid was added thereto to adjust pH to 2, and the mixturewas extracted with ethyl acetate. The organic layer was successivelywashed with water and brine, and dried over anhydrous magnesium sulfate.The solvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by ethyl acetate) to obtain 148.1mg (0.555 mmol, Yield: 77.1%) of6-chloro-3-(2-methoxy-5-methylphenoxy)-4-pyridazinol (Compound No. 704).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.04-6.91 (3H, m), 6.66 (1H, s), 3.70(3H, s), 2.27 (3H, s). Melting point (° C.): 126-134.

EXAMPLE 176-Chloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}-4-pyridazinol(Compound No. 728) (1) 3-Fluoro-2-methoxybenzaldehyde

To an acetonitrile (50 mL) solution containing 3.01 g (21.5 mmol) ofcommercially available 3-fluoro-2-hydroxybenzaldehyde were added 5.92 g(42.8 mmol) of potassium carbonate and 6.66 mL (107 mmol) of methyliodide, and the mixture was stirred at 90° C. for 3 hours. Afterallowing to stand at room temperature overnight, the reaction mixturewas poured into water, and extracted with ethyl acetate. The organiclayer was successively washed with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel column chromatography (Wako gelC-100, hexane-ethyl acetate, gradient) to obtain 3.22 g of a crudeproduct of 3-fluoro-2-methoxybenzaldehyde.

(2) 1-Fluoro-2-methoxy-3-vinylbenzene

Under nitrogen atmosphere, 273.2 mg (6.83 mmol) of 60% sodium hydridewashed with hexane was suspended in dry dimethylsulfoxide (3 mL), andthe suspension was stirred at 85° C. for 30 minutes, cooled to roomtemperature and then, in an ice bath, a dry dimethylsulfoxide (8 mL)solution containing 2.44 g (6.83 mmol) of methyl(triphenyl)phosphoniumbromide was gradually added dropwise. After stirring at room temperaturefor 30 minutes, a dry dimethylsulfoxide (5 mL) solution containing 877.4mg of a crude product of 3-fluoro-2-methoxybenzaldehyde obtained in (1)was added dropwise, and the mixture was stirred at room temperature for30 minutes. The reaction mixture was poured into water, and extractedwith ethyl acetate. The organic layer was washed successively with waterand brine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate, gradient) toobtain 0.38 g (2.5 mmol) of 1-fluoro-2-methoxy-3-vinylbenzene.

(3) 1-Cyclopropyl-3-fluoro-2-methoxybenzene

Under nitrogen atmosphere, dry diethyl ether (5 mL) was charged in a dryflask, 9.20 mL (9.20 mmol) of diethyl-zinc (1 mol/L hexane solution) wasthen added dropwise, and a dry diethyl ether (10 mL) solution containing0.56 g (3.7 mmol) of 1-fluoro-2-methoxy-3-vinylbenzene obtained in (2)was added dropwise thereto. After stirring at room temperature for 5minutes, 1.48 mL (18.4 mmol) of diiodomethane was added dropwisethereto, and the resulting mixture was refluxed for 5 hours. Aftercooling to room temperature, 9.20 mL (9.20 mmol) of diethylzinc (1 mol/Lhexane solution) and 1.48 mL (18.4 mmol) of diiodomethane wereadditionally added, and the resulting mixture was again refluxed for 4hours. After allowing to stand at room temperature overnight, thereaction mixture was poured into a saturated aqueous ammonium chloridesolution. To the mixture was added a saturated aqueous sodium hydrogencarbonate solution and after stirring for 30 minutes, and the mixturewas extracted with diethyl ether. The organic layer was successivelywashed with water and brine, and dried over anhydrous magnesium sulfate.The solvent was removed, and the obtained residue was purified by silicagel column chromatography (Wako gel C-100, hexane-ethyl acetate,gradient) to obtain 0.82 g of a crude product of1-cyclopropyl-3-fluoro-2-methoxybenzene.

(4) 6-Chloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}pyridazine1-oxide (Step B-2)

Under nitrogen atmosphere, 288.8 mg (7.22 mmol) of 60% sodium hydridewas suspended in dry N,N-dimethylformamide (3 mL), and 0.55 mL (7.5mmol) of ethanethiol was gradually added dropwise to the suspension.After stirring for 15 minutes, a dry N,N-dimethylformamide (6 mL)solution containing 402.1 mg of a crude product of1-cyclopropyl-3-fluoro-2-methoxybenzene obtained in (3) was addeddropwise thereto, and the resulting mixture was stirred at 160° C. for 5hours. After allowing to stand at room temperature overnight, 1 mol/Laqueous potassium hydroxide solution and diethyl ether were added to thereaction mixture. The aqueous layer was separated, washed with diethylether, and added thereto diluted hydrochloric acid to adjust pH to 2.The mixture was extracted with diethyl ether, ether extracts werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 3 plates were used, developed byethyl acetate:hexane=4:1) to obtain 299.9 mg of a mixture.

In a mixed solvent of 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL)was dissolved 152.7 mg of the mixture, 116.1 mg (1.03 mmol) of potassiumtert-butoxide was added to the solution, then 162.6 mg (0.988 mmol) of3,6-dichloropyridazine 1-oxide was added thereto, and the resultingmixture was stirred at room temperature over-night. The reaction mixturewas poured into water, and extracted with ethyl acetate. The organiclayer was successively washed with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 3 plates were used, developed byethyl acetate:hexane=2:1) to obtain 46.6 mg (0.144 mmol) of6-chloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}pyridazine1-oxide.

(5)4,6-Dichloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}pyridazine(Step B-3)

A phosphorus oxychloride (0.5 mL) solution containing 46.6 mg (0.144mmol) of6-chloro-3-{2-[1-(ethylsulfanyl)-ethyl]-6-fluorophenoxy}pyridazine1-oxide obtained in (4) was stirred at room temperature overnight. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layer was successively washed with water and brine,and dried over anhydrous magnesium sulfate. The solvent was distilledoff and the obtained residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05744, 1 plate was used,developed by ethyl acetate:hexane=4:1) to obtain 9.8 mg (0.028 mmol,Yield: 19%) of4,6-dichloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}pyridazine.

(6)6-Chloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}-4-pyridazinol(Compound No. 728, Step B-4)

In a mixed solvent of 1,4-dioxane (1 mL) and dimethylsulfoxide (1 mL)was dissolved 9.8 mg (0.028 mmol) of4,6-dichloro-3-{2-[l-(ethylsulfanyl)ethyl]-6-fluorophenoxy}pyridazineobtained in (5), 0.07 mL (0.14 mmol) of 2 mol/L aqueous sodium hydroxidesolution was added to the solution, and the resulting mixture wasstirred at room temperature overnight. The reaction mixture was pouredinto water, diluted hydrochloric acid was added thereto to adjust pH to2, and the mixture was extracted with ethyl acetate. The organic layerwas successively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05744, 1 plate was used, developed by ethyl acetate)to obtain 2.2 mg (0.0067 mmol, Yield: 24%) of6-chloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}-4-pyridazinol(Compound No. 728).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.42 (1H, d, J=8.1 Hz), 7.26-7.15 (1H,m), 7.07-6.97 (1H, m), 6.46 (1H, s), 4.33 (1H, q, J=7.0 Hz), 2.42-2.20(2H, m), 1.43 (3H, d, J=7.0 Hz), 1.02 (3H, t, J=7.0 Hz). Appearance:amorphous.

EXAMPLE 18 6-Chloro-3-(2-chloro-6-isopropylphenoxy)-4-pyridazinol(Compound No. 738) (1) 1-Isopropyl-2-[(2-methoxyethoxy)methoxy]benzene

In dry tetrahydrofuran (60 mL) was suspended 4.80 g (120 mmol) of 60%sodium hydride, and a dry tetrahydrofuran (80 mL) solution containing13.6 g (100 mmol) of 2-isopropylphenol was added dropwise to thesuspension at 0° C. After stirring at 0° C. for 10 minutes, a drytetrahydrofuran (80 mL) solution containing 14.9 g (119 mmol) of2-methoxyethoxymethyl chloride was added dropwise thereto. The reactionmixture was stirred in an ice bath for 2 hours, poured into ice-coldwater (250 mL), and extracted with ethyl acetate. The organic layerswere combined, washed succeccively with 1 mol/L aqueous sodium hydroxidesolution and brine, and dried over anhydrous sodium sulfate. The solventwas removed, and the residue was purified by silica gel columnchromatography (eluted with hexane:ethyl acetate=50:1) to obtain 18.1 g(80.8 mmol, Yield: 80.8%) of1-isopropyl-2-[(2-methoxyethoxy)methoxy]benzene.

(2) 1-Chloro-3-isopropyl-2-[(2-methoxyethoxy)methoxy]-benzene

In a dry ether (100 mL) was dissolved 8.00 g (35.7 mmol) of1-isopropyl-2-[(2-methoxyethoxy)methoxy]benzene obtained in (1), and34.4 mL (55.0 mmol) of n-butyl lithium-hexane solution (1.60M) was addedto the solution in an ice bath (reaction solution temperature: 5-10°C.), and the mixture was stirred in an ice bath for 5 hours. To themixture was passed through 2.51 g (35.4 mmol) of a chlorine gas whilekeeping the reaction solution temperature to 5-10° C. The reactionmixture was stirred in an ice bath for 1 hour, poured into 1 mol/Lhydrochloric acid (300 mL), and extracted with ether. The organic layerswere combined, dried over anhydrous sodium sulfate, and the solvent wasremoved. The residue was purified by silica gel column chromatography(eluted with hexane:ethyl acetate=100:1) to obtain 4.38 g (16.9 mmol,Yield: 47.3%) of1-chloro-3-isopropyl-2-[(2-methoxyethoxy)methoxy]benzene.

(3) 2-Chloro-6-isopropylphenol

In dichloromethane (15 mL) was dissolved 4.38 g (16.9 mmol) of1-chloro-3-isopropyl-2-[(2-methoxyethoxy)methoxy]-benzene obtained in(2), 2.70 g (23.7 mmol) of trifluoroacetic acid was added to thesolution, and the resulting mixture was stirred at room temperatureovernight. The reaction mixture was poured into 1 mol/L hydrochloricacid, and extracted with ethyl acetate. The organic layers werecombined, and dried over anhydrous sodium sulfate. The solvent wasremoved, and the residue was purified by silica gel columnchromatography (eluted with hexane) to obtain 2.50 g (14.7 mmol, Yield:87.0%) of 2-chloro-6-isopropylphenol.

(4) 3-Chloro-6-(2-chloro-6-isopropylphenoxy)pyridazine (Step A-1)

1.98 g (17.7 mmol) of potassium tert-butoxide, 1,4-dioxane (100 mL) and2.50 g (14.7 mmol) of 2-chloro-6-isopropylphenol obtained in (3) weremixed, and the mixture was stirred at room temperature for 20 minutes.To the mixture was added 2.18 g (14.6 mmol) of 3,6-dichloropyridazineand the mixture was refluxed for 4 hours. To the reaction mixture wasfurther added 0.50 g (4.5 mmol) of potassium tert-butoxide, and themixture was refluxed for further 3 hours. The reaction mixture wasallowed to stand for cooling, poured into 1N hydrochloric acid (100 mL),and extracted with ethyl acetate. The organic layers were combined,washed successively with water and brine, and dried over anhydroussodium sulfate. The solvent was removed, and the obtained residue waspurified by silica gel column chromatography (hexane:ethyl acetate,gradient) to obtain 3.18 g (11.2 mmol, Yield: 76.2%) of3-chloro-6-(2-chloro-6-isopropylphenoxy)pyridazine.

(5) Mixture of 6-chloro-3-(2-chloro-6-isopropylphenoxy)-pyridazine1-oxide and 3-chloro-6-(2-chloro-6-isopropylphenoxy)pyridazine 1-oxide(Step C-1)

In dry dichloromethane (90 mL) was dissolved 3.17 g (11.2 mmol) of3-chloro-6-(2-chloro-6-isopropylphenoxy)-pyridazine obtained in (4),2.90 g (13.4-14.3 mmol) of 80-85% m-chloroperbenzoic acid was added tothe solution, and the mixture was refluxed for 13 hours. The reactionmixture was poured into 1N aqueous sodium hydroxide solution, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (hexane:ethyl acetate, gradient) toobtain 2.82 g (9.43 mmol, Yield: 84.2%) of a mixture of6-chloro-3-(2-chloro-6-isopropylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-chloro-6-isopropylphenoxy)pyridazine 1-oxide.

(6) Mixture of 4,6-dichloro-3-(2-chloro-6-isopropylphenoxy)pyridazineand 3,4-dichloro-6-(2-chloro-6-isopropylphenoxy)pyridazine (Step C-2)

2.80 g (9.36 mmol) of a mixture of6-chloro-3-(2-chloro-6-isopropylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-chloro-6-isopropylphenoxy)pyridazine 1-oxide obtained in(5) was mixed with 17.5 mL (189 mmol) of phosphorus oxychloride, and themixture was refluxed for 2 hours and 30 minutes. The reaction mixturewas allowed to stand for cooling, poured into ice-cold water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (hexane:ethyl acetate=20:1) toobtain 0.850 g (2.67 mmol, m.p. 90-91° C.) of4,6-dichloro-3-(2-chloro-6-isopropylphenoxy)pyridazine, and 1.78 g (5.60mmol) of a mixture of4,6-dichloro-3-(2-chloro-6-isopropylphenoxy)pyridazine and3,4-dichloro-6-(2-chloro-6-isopropylphenoxy)pyridazine.

(7) 6-Chloro-3-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine and3-chloro-6-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine (Step C-3)

To methanol (10 mL) was added 0.080 g (3.5 mmol) of sodium, and themixture was stirred at room temperature for 30 minutes. To the mixturewas added 0.830 g (2.61 mmol) of4,6-dichloro-3-(2-chloro-6-isopropylphenoxy)pyridazine obtained in (6),and the mixture was stirred at room temperature for 2 hours. Thereaction mixture was poured into ice-cold water, and extracted withethyl acetate. The organic layers were combined, dried over anhydroussodium sulfate, and the solvent was removed. The obtained residue waspurified by silica gel column chromatography (hexane: ethylacetate=10:1), washed with hexane and crystallized to obtain 0.720 g(2.30 mmol, Yield: 88.1%) of6-chloro-3-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine. On theother hand, 1.78 g (5.60 mmol) of the mixture of4,6-dichloro-3-(2-chloro-6-isopropylphenoxy)pyridazine and3,4-dichloro-6-(2-chloro-6-isopropylphenoxy)pyridazine was reacted inthe same manner as mentioned above to obtain 1.25 g (3.99 mmol, Yield:71.3%) of 6-chloro-3-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazineand 0.300 g (0.958 mmol, Yield: 17.1%) of3-chloro-6-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine.

(8) 6-Chloro-3-(2-chloro-6-isopropylphenoxy)-4-pyridazinol (Compound No.738, Step C-4)

In dimethylsulfoxide (13 mL) was dissolved 1.46 g (4.66 mmol) of6-chloro-3-(2-chloro-6-isopropylphenoxy)-4-methoxypyridazine obtained in(7), 3 mL (6.0 mmol) of 2 mol/L aqueous sodium hydroxide solution wasadded to the solution, and the resulting mixture was stirred at 80° C.for 3 hours. The reaction mixture was poured into water, and made acidicwith hydrochloric acid. The precipitated solid was collected byfiltration, washed with water, and air dried.6-Chloro-3-(2-chloro-6-isopropylphenoxy)-4-pyridazinol (Compound No.738) was obtained in an amount of 1.33 g (4.45 mmol, Yield: 95.5%).

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 7.40-7.05 (3H, m), 6.70 (1H, s), 2.98(1H, septet, J=6.2 Hz), 1.13 (6H, d, J=6.2 Hz). Melting point (° C.):218-233.

EXAMPLE 19 3-(2-Bromo-6-isopropylphenoxy)-6-chloro-4-pyridazinol(Compound No. 760) (1)1-Bromo-3-isopropyl-2-[(2-methoxyethoxy)methoxy]benzene

In dry ether (100 mL) was dissolved 5.18 g (23.1 mmol) of1-isopropyl-2-[(2-methoxyethoxy)methoxy]benzene obtained in Example18(1), 22.3 mL (35.7 mmol) of n-butyl lithium-hexane solution (1.60M)was added dropwise to the solution in an ice bath (reaction solutiontemperature: 5-10° C.), and the mixture was stirred in an ice bath for 5hours. To the reaction mixture was added 8.20 g (69.7 mmol) of 90%cyanogen bromide while maintaining the reaction solution temperature to5-10° C. The reaction mixture was stirred in an ice bath for 2 hours,poured into ice-cold water (300 mL), and extracted with ether. Theorganic layers were combined, dried over anhydrous sodium sulfate, andthe solvent was removed. The residue was purified by silica gel columnchromatography (eluted with hexane:ethyl acetate=100:1) to obtain 3.40 g(11.2 mmol, Yield: 48.5%) of1-bromo-3-isopropyl-2-[(2-methoxyethoxy)-methoxy]benzene.

(2) 2-Bromo-6-isopropylphenol

In dichloromethane (10 mL) was dissolved 3.40 g (11.2 mmol) of1-bromo-3-isopropyl-2-[(2-methoxyethoxy)methoxy]-benzene obtained in(1), 2.50 g (21.9 mmol) of trifluoroacetic acid was added to thesolution, and the mixture was stirred at room temperature overnight. Thereaction mixture was poured into 1 mol/L hydrochloric acid, andextracted with ethyl acetate. The organic layers were combined, anddried over anhydrous sodium sulfate. The solvent was removed, and theresidue was purified by silica gel column chromatography (eluted withhexane) to obtain 2.27 g (10.6 mmol, Yield: 94.6%) of2-bromo-6-isopropylphenol.

(3) 3-(2-Bromo-6-isopropylphenoxy)-6-chloropyridazine (Step A-1)

1.52 g (13.6 mmol) of potassium tert-butoxide, 1,4-dioxane (60 mL) and2.27 g (10.6 mmol) of 2-bromo-6-isopropylphenol obtained in (2) weremixed, and the mixture was stirred at room temperature for 20 minutes.To the mixture was added 1.58 g (10.6 mmol) of 3,6-dichloropyridazine,and the resulting mixture was refluxed for 7 hours and 20 minutes. Thereaction mixture was allowed to stand for cooling, poured into ice-coldwater (110 mL), and extracted with ethyl acetate. The organic layerswere combined, washed with brine, and dried over anhydrous sodiumsulfate. The solvent was removed, the obtained residue wasrecrystallized (from isopropyl ether), then, purified by silica gelcolumn chromatography (hexane:ethyl acetate, gradient) to obtain 2.68 g(8.17 mmol, Yield: 77.1%) of3-(2-bromo-6-isopropylphenoxy)-6-chloropyridazine.

(4) Mixture of 3-(2-bromo-6-isopropylphenoxy)-6-chloropyridazine 1-oxideand 6-(2-bromo-6-isopropylphenoxy)-3-chloropyridazine 1-oxide (Step C-1)

In dry dichloromethane (35 mL) was dissolved 2.68 g (8.17 mmol) of3-(2-bromo-6-isopropylphenoxy)-6-chloropyridazine obtained in (3), 2.12g (9.80-10.4 mmol) of 80-85% m-chloroperbenzoic acid was added to thesolution, and the mixture was refluxed for 12 hours and 30 minutes. Thereaction mixture was poured into 1 mol/L aqueous sodium hydroxidesolution, and extracted with ethyl acetate. The organic layers werecombined, washed with brine, and dried over anhydrous sodium sulfate.The solvent was removed, and the obtained residue was purified by silicagel column chromatography (hexane:ethyl acetate=5:1) to obtain 2.26 g(6.57 mmol, Yield: 80.4%) of a mixture of3-(2-bromo-6-isopropylphenoxy)-6-chloropyridazine 1-oxide and6-(2-bromo-6-isopropylphenoxy)-3-chloropyridazine 1-oxide.

(5) Mixture of 3-(2-bromo-6-isopropylphenoxy)-4,6-dichloropyridazine and6-(2-bromo-6-isopropylphenoxy)-3,4-dichloropyridazine (Step C-2)

A mixture of 2.14 g (6.22 mmol) of3-(2-bromo-6-isopropylphenoxy)-6-chloropyridazine 1-oxide and6-(2-bromo-6-isopropylphenoxy)-3-chloropyridazine 1-oxide obtained in(4) was mixed with 11.6 mL (125 mmol) of phosphorus oxychloride, and theresulting mixture was refluxed for 3 hours. The reaction mixture wascooled by allowing to stand, poured into ice-cold water, and extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with 1 mol/L of an aqueous sodium hydroxide solution, waterand brine, and dried over anhydrous sodium sulfate. The solvent wasremoved, and the obtained residue was purified by silica gel columnchromatography (hexane:ethyl acetate=20:1) to obtain 2.22 g (6.13 mmol,Yield: 98.6%) of a mixture of3-(2-bromo-6-isopropylphenoxy)-4,6-dichloropyridazine and6-(2-bromo-6-isopropylphenoxy)-3,4-dichloropyridazine.

(6) 3-(2-Bromo-6-isopropylphenoxy)-6-chloro-4-methoxypyridazine(Step-C-3)

To methanol (20 mL) was added 0.180 g (7.8 mmol) of sodium, and themixture was stirred at room temperature for 30 minutes. To the mixturewas added 2.22 g (6.13 mmol) of a mixture of3-(2-bromo-6-isopropylphenoxy)-4,6-dichloropyridazine and6-(2-bromo-6-isopropylphenoxy)-3,4-dichloropyridazine obtained in (5)and the resulting mixture was stirred at room temperature for 4 hours.The reaction mixture was poured into ice-cold water, and extracted withethyl acetate. The organic layers were combined, washed with brine, anddried over anhydrous sodium sulfate. The solvent was removed, and theobtained residue was purified by silica gel column chromatography(hexane:ethyl acetate=15:1), and washed with hexane to crystallize toobtain 1.48 g (4.13 mmol, Yield: 67.4%) of3-(2-bromo-6-isopropylphenoxy)-6-chloro-4-methoxypyridazine. Also, 0.21g (0.59 mmol, Yield: 9.6%) of6-(2-bromo-6-isopropylphenoxy)-3-chloro-4-methoxypyridazine wassimultaneously obtained.

(7) 3-(2-Bromo-6-isopropylphenoxy)-6-chloro-4-pyridazinol (Compound No.760, Step C-4)

In dimethylsulfoxide (10 mL) was dissolved 0.72 g (2.0 mmol) of3-(2-bromo-6-isopropylphenoxy)-6-chloro-4-methoxypyridazine obtained in(6), an aqueous sodium hydroxide solution (prepared by dissolving 100 mgof sodium hydroxide in 1.5 mL of water, 2.4 mmol) was added to thesolution, and the resulting mixture was stirred at 80° C. for 3 hours.The reaction mixture was poured into water, and made acidic byhydrochloric acid. The precipitated solid was collected by filtration,washed with water, and air-dried. Thus, 0.56 g (1.6 mmol, Yield: 80%) of3-(2-bromo-6-isopropylphenoxy)-6-chloro-4-pyridazinol (Compound No. 760)was obtained.

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.70-7.00 (3H, m), 6.89 (1H, s), 2.94(1H, septet, J=7.0 Hz), 1.16 (6H, d, J=7.0 Hz). Melting point (° C.):232-253 (dec.).

EXAMPLE 20 3-(2-Bromo-6-tert-butylphenoxy)-6-chloro-4-pyridazinol(Compound No. 761) (1) tert-Butyl-2-[(2-methoxyethoxy)methoxy]benzene

In dry tetrahydrofuran (25 mL) was suspended 4.80 g (120 mmol) of 60%sodium hydride, and a dry tetrahydrofuran (80 mL) solution containing15.0 g (100 mmol) of 2-tert-butylphenol was added dropwise to thissuspension at 0° C. After stirring the mixture at 0° C. for 10 minutes,a dry tetrahydrofuran (80 mL) solution containing 14.9 g (119 mmol) of2-methoxyethoxymethyl chloride was added dropwise to the mixture. Thereaction mixture was stirred in an ice bath for 4 hours and 30 minutes,and allowed to stand at room temperature overnight. To the reactionmixture were further added 1.20 g (30 mmol) of 60% sodium hydride and3.8 g (30 mmol) of 2-methoxyethoxymethyl chloride at 0° C., and themixture was stirred at 0° C. for 7 hours. The reaction mixture waspoured into ice-cold water (250 mL), and extracted with ethyl acetate.The organic layers were combined, washed with 2N aqueous sodiumhydroxide solution and brine, and dried over anhydrous sodium sulfate.The solvent was removed, and the residue was purified by silica gelcolumn chromatography (eluted with hexane:ethyl acetate=20:1) to obtain19.7 g (82.8 mmol, Yield: 82.8%) oftert-butyl-2-[(2-methoxyethoxy)methoxy]benzene.

(2) 1-Bromo-3-tert-butyl-2-[(2-methoxyethoxy)methoxy]-benzene

In dry ether (120 mL) was dissolved 10.0 g (42.0 mmol) oftert-butyl-2-[(2-methoxyethoxy)methoxy]benzene obtained in (1), 42.1 mL(64.4 mmol) of n-butyl lithium-hexane solution (1.53M) was addeddropwise to the solution in an ice bath, and the mixture was stirred inan ice bath for 3 hours. To the mixture was added dropwise a dry ether(20 mL) solution containing 14.8 g (126 mmol) of 90% cyanogen bromide.The reaction mixture was stirred in an ice bath for 3 hours, poured intoice-cold water (300 mL), and extracted with ether. The organic layerswere combined, washed with brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the residue was purified by silicagel column chromatography (eluted with hexane:ethyl acetate=20:1) toobtain 8.48 g (26.8 mmol, Yield: 63.8%) of1-bromo-3-tert-butyl-2-[(2-methoxyethoxy)methoxy]benzene.

(3) 2-Bromo-6-tert-butylphenol

In dichloromethane (30 mL) was dissolved 8.38 g (26.4 mmol) of1-bromo-3-tert-butyl-2-[(2-methoxyethoxy)methoxy]-benzene obtained in(2), a dichloromethane (20 mL) solution containing 9.03 g (79.2 mmol) oftrifluoroacetic acid was added to the solution, and the mixture wasstirred at room temperature overnight. The reaction mixture was pouredinto ice-cold 1 mol/L of hydrochloric acid, and extracted with ethylacetate. The organic layers were combined, washed with brine, and driedover anhydrous sodium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (eluted with hexane) toobtain 5.68 g (24.8 mmol, Yield: 93.9%) of 2-bromo-6-tert-butylphenol.

(4) 3-(2-Bromo-6-tert-butylphenoxy)-6-fluoropyridazine (Step A-1)

In 1,4-dioxane (40 mL) was dissolved 4.84 g (21.1 mmol) of2-bromo-6-tert-butylphenol obtained in (3), 3.55 g (31.7 mmol) ofpotassium tert-butoxide and 1,4-dioxane (40 mL) were added to thesolution, and the mixture was stirred at room temperature for 15minutes. To the mixture was added 2.45 g (21.1 mmol) of3,6-difluoropyridazine and the resulting mixture was refluxed for 24hours with stirring. The reaction mixture was allowed to stand forcooling, poured into ice-cold water, and extracted with ethyl acetate.The organic layers were combined, washed with brine, and dried overanhydrous sodium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel column chromatography (hexane: ethylacetate, gradient) to obtain 1.70 g (5.23 mmol, Yield: 24.8%) of3-(2-bromo-6-tert-butylphenoxy)-6-fluoropyridazine.

(5) 6-(2-Bromo-6-tert-butylphenoxy)-3-pyridazinol

1.04 g (10.6 mmol) of potassium acetate was added to a mixture of aceticacid (9 mL) and 1.70 g (5.23 mmol) of3-(2-bromo-6-tert-butylphenoxy)-6-fluoropyridazine obtained in (4), andthe resulting mixture was stirred at 130-140° C. for 3 hours. Thereaction mixture was allowed to stand for cooling, poured into ice-coldwater, and extracted with ethyl acetate. The organic layers werecombined, washed with brine, and dried over anhydrous sodium sulfate.The solvent was removed, and the obtained residue was washed withbenzene to obtain 1.54 g (4.77 mmol, Yield: 91.2%, m.p. 255-257° C.) of6-(2-bromo-6-tert-butylphenoxy)-3-pyridazinol.

(6) 3-(2-Bromo-6-tert-butylphenoxy)-6-chloropyridazine

1.54 g (4.77 mmol) of 6-(2-bromo-6-tert-butylphenoxy)-3-pyridazinolobtained in (5) was mixed with 15 mL (162 mmol) of phosphorusoxychloride, and the mixture was refluxed for 70 minutes. Phosphorusoxychloride was removed from the reaction mixture by distillation, thereaction mixture was poured into ice-cold water, and extracted withethyl acetate. The organic layers were combined, washed with brine, anddried over anhydrous sodium sulfate. The solvent was removed to obtain1.55 g (4.53 mmol, Yield: 95.0%) of3-(2-bromo-6-tert-butylphenoxy)-6-chloropyridazine.

(7) Mixture of 3-(2-bromo-6-tert-butylphenoxy)-6-chloropyridazine1-oxide and 6-(2-bromo-6-tert-butylphenoxy)-3-chloropyridazine 1-oxide(Step C-1)

In dry dichloromethane (20 mL) was dissolved 1.42 g (4.15 mmol) of3-(2-bromo-6-tert-butylphenoxy)-6-chloropyridazine obtained in (6), adry dichloromethane (10 mL) solution containing 1.08 g (4.99 mmol) of80% m-chloroperbenzoic acid was added to the solution, and the mixturewas refluxed for 20 hours. To the reaction mixture was additionallyadded 0.275 g (1.27 mmol) of 80% m-chloroperbenzoic acid, and afterrefluxing for 3 hours and 30 minutes, the reaction mixture was pouredinto 1 mol/L aqueous sodium hydroxide solution, and extracted with ethylacetate. The organic layers were combined, washed with brine, and driedover anhydrous sodium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel column chromatography (hexane: ethylacetate=10:1) to obtain 0.704 g (1.97 mmol, Yield: 47.5%) of a mixtureof 3-(2-bromo-6-tert-butylphenoxy)-6-chloropyridazine 1-oxide and6-(2-bromo-6-tert-butylphenoxy)-3-chloropyridazine 1-oxide.

(8) 3-(2-Bromo-6-tert-butylphenoxy)-4,6-dichloropyridazine and6-(2-bromo-6-tert-butylphenoxy)-3,4-dichloropyridazine (Step C-2)

0.704 g (1.97 mmol) of a mixture of3-(2-bromo-6-tert-butylphenoxy)-6-chloropyridazine 1-oxide and6-(2-bromo-6-tert-butylphenoxy)-3-chloropyridazine 1-oxide obtained in(7) was mixed with 5 mL (54 mmol) of phosphorus oxychloride, and theresulting mixture was refluxed for 2 hours. The reaction mixture wasallowed to stand for cooling, poured into ice-cold water, and extractedwith ethyl acetate. The organic layers were combined, washed with brine,and dried over anhydrous sodium sulfate. The solvent was removed, andthe obtained residue was purified by silica gel column chromatography(hexane:ethyl acetate=20:1) to obtain 0.474 g (1.26 mmol, Yield: 64.0%)of 3-(2-bromo-6-tert-butylphenoxy)-4,6-dichloropyridazine and 0.119 g(0.316 mmol, Yield: 16.0%) of6-(2-bromo-6-tert-butylphenoxy)-3,4-dichloropyridazine.

(9) 3-(2-Bromo-6-tert-butylphenoxy)-6-chloro-4-methoxypyridazine (StepC-3)

In methanol (10 mL) was dissolved 0.443 g (1.18 mmol) of3-(2-bromo-6-tert-butylphenoxy)-4,6-dichloropyridazine obtained in (8),and 0.545 g (2.83 mmol) of 28% sodium methoxide-methanol solution andmethanol (5 mL) were added to the solution, and the resulting mixturewas stirred at room temperature for 80 minutes. To the reaction mixturewas additionally added 0.10 g (0.52 mmol) of 28% sodiummethoxide-methanol solution, after stirring at room temperature for 2hours, 0.15 g (0.78 mmol) of 28% sodium methoxide-methanol solution wasfurther additionally added to the mixture and the resulting mixture wasstirred at room temperature overnight. The reaction mixture was pouredinto ice-cold water, and extracted with ethyl acetate. The organiclayers were combined, washed with brine, and dried over anhydrous sodiumsulfate. The solvent was removed to obtain 0.428 g (1.15 mmol, Yield:97.5%) of 3-(2-bromo-6-tert-butylphenoxy)-6-chloro-4-methoxypyridazine:

(10) 3-(2-Bromo-6-tert-butylphenoxy)-6-chloro-4-pyridazinol (CompoundNo. 761, Step C-4)

In dimethylsulfoxide (5 mL) was dissolved 0.395 g (1.06 mmol) of3-(2-bromo-6-tert-butylphenoxy)-6-chloro-4-methoxypyridazine obtained in(9), aqueous sodium hydroxide solution (prepared by dissolving 50.8 mgof sodium hydroxide in 3 mL of water, 1.27 mmol) was added to thesolution, and the resulting mixture was stirred at 80° C. for 3 hours.Aqueous sodium hydroxide solution (prepared by dissolving 42 mg ofsodium hydroxide in 3 mL of water, 1.1 mmol) and dimethylsulfoxide (10mL) were additionally added thereto, and the mixture was further stirredat 80° C. for 5 hours. After cooling by allowing to stand, the reactionmixture was poured into ice-cold water, and made acidic by hydrochloricacid. The precipitated solid was collected by filtration, washedsuccessively with water, hexane and isopropyl ether, and air-dried.0.309 g (0.863 mmol, Yield: 81.4%) of3-(2-bromo-6-tert-butylphenoxy)-6-chloro-4-pyridazinol (Compound No.761) was obtained.

¹H-NMR (270 MHz, CDCl₃) δ ppm: 9.55 (1H, brs), 7.47 (1H, dd, J=8.1, 1.7Hz), 7.41 (1H, dd, J=8.1, 1.7 Hz), 7.08 (1H, t, J=8.1 Hz), 6.58 (1H,brs), 1.34 (9H, s). Melting point (° C.): 240-247.

EXAMPLE 21 6-Chloro-3-(2,6-dimethylphenoxy)-4-pyridazinol (Compound No.801) (1) 6-Chloro-3-(2,6-dimethylphenoxy)pyridazine 1-oxide (Step B-2)

268 mg (2.20 mmol) of 2,6-dimethylphenol, 1,4-dioxane (3 mL) anddimethylsulfoxide (3 mL) were mixed, 270 mg (2.41 mmol) of potassiumtert-butoxide was added to the mixture in an ice bath, and the resultingmixture was stirred for 10 minutes. To the mixture was added 370 mg(2.24 mmol) of 3,6-dichloropyridazine 1-oxide, and the resulting mixturewas stirred at room temperature for 10 hours and allowed to stand for 2days. The reaction mixture was poured into ice-cold water, and extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the residue was purified by silicagel column chromatography (hexane: ethyl acetate, gradient) to obtain350 mg (1.39 mmol, Yield: 63.1%) of6-chloro-3-(2,6-dimethylphenoxy)pyridazine 1-oxide.

(2) 4,6-Dichloro-3-(2,6-dimethylphenoxy)pyridazine (Step B-3)

330 mg (1.31 mmol) of 6-chloro-3-(2,6-dimethylphenoxy)pyridazine 1-oxideobtained in (1) was mixed with dichloromethane (0.6 mL) and phosphorusoxychloride 0.60 mL (6.5 mmol), and the mixture was stirred for 1 hourand allowed to stand for further 5 days. The reaction mixture was pouredinto ice-cold water, and extracted with ethyl acetate. The organiclayers were combined, washed successively with water and brine, anddried over anhydrous sodium sulfate. The solvent was removed, and theresidue was purified by silica gel column chromatography (hexane: ethylacetate, gradient) to obtain 322 mg (1.20 mmol, Yield: 91.6%) of4,6-dichloro-3-(2,6-dimethylphenoxy)-pyridazine.

(3) 6-Chloro-3-(2,6-dimethylphenoxy)-4-pyridazinol (Compound No. 801,Step B-4)

In dimethylsulfoxide (8 mL) was dissolved 300 mg (1.12 mmol) of4,6-dichloro-3-(2,6-dimethylphenoxy)-pyridazine obtained in (2), 0.80 mL(2.0 mmol) of 10% (W/V) aqueous sodium hydroxide solution was added tothe solution, and the resulting mixture was stirred at room temperatureovernight. To the mixture was further added. 0.80 mL (2.0 mmol) of 10%(W/V) aqueous sodium hydroxide solution, and after disappearance of thestarting materials, the reaction mixture was poured into ice-cold water.The mixture was made acidic with hydrochloric acid, and then, extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the residue was purified by silicagel column chromatography (hexane:ethyl acetate, gradient) and purifiedby preparative thin-layer chromatography (available from Merck Co.,1.05744, developed by dichloromethane: methanol=9:1) to obtain 128 mg(0.510 mmol, Yield: 45.5%) of6-chloro-3-(2,6-dimethylphenoxy)-4-pyridazinol (Compound No. 801).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.18-7.05 (3H, m), 6.83 (1H, s), 2.05(6H, s). Melting point (° C.): 214-215.

EXAMPLE 22 3-(2-tert-Butyl-6-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 805) (1)3-(2-tert-Butyl-6-methylphenoxy)-6-chloropyridazine (Step A-1)

17.5 g (107 mmol) of 2-tert-butyl-6-methylphenol, 11.9 g (106 mmol) ofpotassium tert-butoxide and 1,4-dioxane (250 mL) were mixed, and themixture was stirred at room temperature for 30 minutes. To the mixturewas added 15.0 g (101 mmol) of 2,6-dichloropyridazine and the resultingmixture was stirred at 100° C. for 3 hours and 15 minutes. The reactionmixture was poured into ice water, and extracted with ethyl acetate. Theorganic layer was washed successively with water and brine, and driedover anhydrous sodium sulfate. The solvent was removed, and the residuewas crystallized form isopropyl ether to obtain 15.3 g (55.2 mmol,Yield: 54.6%) of 3-(2-tert-butyl-6-methylphenoxy)-6-chloropyridazine.

(2) 3-(2-tert-Butyl-6-methylphenoxy)-6-chloropyridazine 1-oxide (StepC-1)

8.00 g (28.9 mmol) of3-(2-tert-butyl-6-methylphenoxy)-6-chloropyridazine obtained in (1) wasmixed with dry dichloromethane (200 mL) and 8.50 g (34.4 mmol) of 70%m-chloroperbenzoic acid, and the mixture was stirred at room temperaturefor 4 days. The reaction mixture was poured into an ice-coled saturatedaqueous sodium sulfite solution, and extracted with dichloromethane. Theorganic layers were combined, washed successively with water and brine,and dried over anhydrous sodium sulfate. The solvent was removed, andthe residue was crystallized from a mixed solvent of ether-hexane orpurified by silica gel column chromatography to obtain 7.04 g (24.0mmol, Yield: 83.0%) of3-(2-tert-butyl-6-methylphenoxy)-6-chloropyridazine 1-oxide.

(3) 3-(2-tert-Butyl-6-methylphenoxy)-4,6-dichloropyridazine (Step C-2)

1.00 g (3.41 mmol) of3-(2-tert-butyl-6-methylphenoxy)-6-chloropyridazine 1-oxide obtained in(2) was mixed with chloroform (10 mL) and 0.48 mL (5.2 mmol) ofphosphorus oxychloride, and the mixture was stirred under reflux for 24hours and at room temperature for 2 days. The reaction mixture waspoured into ice-cold water, and extracted with dichloromethane. Theorganic layers were combined, washed successively with a saturatedaqueous sodium hydrogen carbonate solution, water and brine, and driedover anhydrous sodium sulfate. The solvent was removed and the residuewas crystallized from a mixed solvent of ether-hexane to obtain 0.767 g(2.47 mmol, Yield: 72.4%) of3-(2-tert-butyl-6-methylphenoxy)-4,6-dichloropyridazine.

(4) 3-(2-tert-Butyl-6-methylphenoxy)-6-chloro-4-pyridazinol (CompoundNo. 805, Step C-3)

354 mg (1.14 mmol) of3-(2-tert-butyl-6-methylphenoxy)-4,6-dichloropyridazine obtained in (3)was mixed with dimethylsulfoxide (10 mL) and 1.6 mL (1.6 mmol) of 1mol/L aqueous sodium hydroxide solution, and the mixture was stirred atroom temperature for 2 hours and 30 minutes. The reaction mixture waspoured into ice-cold water, and washed with ether. The aqueous layer wasmade acidic with hydrochloric acid, and extracted with ethyl acetate.The organic layer was washed with brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the residue was crystallized froma mixed solvent of ether-hexane to obtain 172 mg (0.587 mmol, Yield:51.5%) of 3-(2-tert-butyl-6-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 805).

¹H-NMR (90 MHz, CDCl₃) δ ppm: 7.35-6.80 (3H, m), 6.50 (1H, s), 1.80 (3H,s), 1.18 (9H, s). Melting point (° C.): 135-136.

EXAMPLE 23 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol(Compound No. 806) (1)6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropyl-6-methylphenoxy)pyridazine 1-oxide (Step B-2)

221 mg (1.49 mmol) of 2-cyclopropyl-6-methylphenol was mixed with1,4-dioxane (2 mL) and dimethylsulfoxide (2 mL), 184 mg (1.64 mmol) ofpotassium tert-butoxide was added to the mixture in an ice bath, and theresulting mixture was stirred for 10 minutes. To the mixture was added258 mg (1.56 mmol) of 3,6-dichloropyridazine 1-oxide, and the resultingmixture was stirred at room temperature for 10 hours, and then, allowedto stand for 3 days. The reaction mixture was poured into ice-coldwater, and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous sodium sulfate. The solvent was removed, and the residue waspurified by silica gel column chromatography (hexane:ethyl acetate,gradient) to obtain 222 mg (0.801 mmol, Yield: 53.8%) of a mixture of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropyl-6-methylphenoxy)pyridazine 1-oxide.

(2) 4,6-Dichloro-3-(2-cyclopropyl-6-methylphenoxy)-pyridazine (Step B-3)

In chloroform (1 mL) was dissolved 210 mg (0.758 mmol) of a mixture of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropyl-6-methylphenoxy)pyridazine 1-oxide obtained in(1), 0.106 mL (1.14 mmol) of phosphorus oxychloride was added to themixture, and after removing almost all the chloroform with anitrogen-stream, the mixture was stirred at room temperature for 2 days.Further, chloroform (2 mL) and 0.150 mL (1.62 mmol) of phosphorusoxychloride were added to the mixture, and after removing almost all thechloroform with a nitrogen stream, the mixture was stirred for 3 hours.The reaction mixture was poured into ice-cold water, and extracted withethyl acetate. The organic layers were combined, washed successivelywith water, brine, and dried over anhydrous sodium sulfate. The solventwas removed, and the residue was purified by silica gel columnchromatography (hexane:ethyl acetate, gradient) to obtain 167 mg (0.566mmol, Yield: 74.7%) of4,6-dichloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazine.

(3) 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CompoundNo. 806, Step B-4)

In dimethylsulfoxide (3 mL) was dissolved 150 mg (0.508 mmol) of4,6-dichloro-3-(2-cyclopropyl-6-methylphenoxy)pyridazine obtained in(2), 0.37 mL (0.925 mmol) of 10% (W/V) aqueous sodium hydroxide solutionwas added to the solution, and the mixture was stirred at roomtemperature for 4 days. The reaction mixture was poured into anice-coled 5% aqueous sodium hydroxide solution, and extracted withether. The aqueous layer was made acidic with hydrochloric acid, andextracted with ether. The organic layer was dried and concentrated. Theresidue was purified by preparative thin-layer chromatography (availablefrom Merck Co., 1.05744, developed by dichloromethane: methanol=20:1) toobtain 114 mg (0.412 mmol, Yield: 81.1%) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (Compound No.806).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.13-7.03 (2H, m), 6.84-6.79 (2H, m),2.06 (3H, s), 1.83-1.68 (1H, m), 0.82-0.72 (2H, m), 0.64-0.51 (2H, m).Melting point (° C.): 201-202.

EXAMPLE 246-Chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]-4-pyridazinol(Compound No. 827) (1)1-(2,2-Dichlorocyclopropyl)-2-methoxy-3-methylbenzene

In chloroform (12 mL) was dissolved 304 mg (2.05 mmol) of2-methoxy-1-methyl-3-vinylbenzene, 5 mL (63 mmol) of 50% aqueous sodiumhydroxide solution was added dropwise to the solution, then, 59.9 mg(0.263 mmol) of benzyl-(triethyl)ammonium chloride was added to themixture, and the resulting mixture was stirred at room temperatureovernight. The reaction mixture was poured into water, and extractedwith chloroform. The organic layer was successively washed with waterand brine, and dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the obtained residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 3 plateswere used, developed by hexane:ethyl acetate=4:1) to obtain 390 mg (1.69mmol, Yield: 82.4%) of1-(2,2-dichlorocyclopropyl)-2-methoxy-3-methylbenzene.

(2) 2-(2,2-Dichlorocyclopropyl)-6-methylphenol

In dichloromethane (5 mL) was dissolved 102 mg (0.442 mmol) of1-(2,2-dichlorocyclopropyl)-2-methoxy-3-methylbenzene obtained in (1),the solution was cooled in an ice bath, and 0.045 mL (0.47 mmol) ofboron tribromide was added dropwise to the solution with stirring. Thereaction mixture was stirred in an ice bath for 2 hours, and then,poured into water and extracted with dichloromethane. The organic layerwas successively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05744, 2 plates were used, developed by hexane:ethylacetate=2:1) to obtain 76.9 mg (0.354 mmol, Yield: 80.1%) of2-(2,2-dichlorocyclopropyl)-6-methylphenol.

(3) 6-Chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]pyridazine1-oxide (Step B-2)

198 mg (0.912 mmol) of 2-(2,2-dichlorocyclopropyl)-6-methylphenolobtained in (2) was mixed with 1,4-dioxane (3 mL) and dimethylsulfoxide(3 mL), 113 mg (1.01 mmol) of potassium tert-butoxide was added to themixture in an ice bath, and the resulting mixture was stirred for 10minutes.

To the mixture was added 151 mg (0.915 mmol) of 3,6-dichloropyridazine1-oxide, and the resulting mixture was stirred at room temperatureovernight. The reaction mixture was poured into ice-cold water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was distilled off and the residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by hexane:ethyl acetate=2:1 threetimes) to obtain 257 mg of a crude product of6-chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]pyridazine1-oxide.

(4)4,6-Dichloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]pyridazine(Step B-3)

257 mg of a crude product of6-chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]pyridazine1-oxide obtained in (3) was mixed with phosphorus oxychloride (3 mL),and the mixture was stirred at room temperature overnight. To thereaction mixture were added water and dichloromethane, and the resultingmixture was stirred for 30 minutes. This mixture was separated, theorganic layer was successively washed with water and brine, and driedover anhydrous magnesium sulfate. The solvent was distilled off and theresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05744, 3 plates were used, developed by hexane:ethylacetate=2:1) to obtain 209 mg (0.574 mmol, Yield from2-(2,2-dichlorocyclopropyl)-6-methylphenol with 2 Steps: 62.9%) of4,6-dichloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]pyridazine.

(5)6-Chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]-4-pyridazinol(Compound No. 827, Step B-4)

209 mg (0.574 mmol)-of4,6-dichloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]pyridazineobtained in (4) was mixed with 1,4-dioxane (3 mL) and dimethylsulfoxide(3 mL), 1.43 mL (2.86 mmol) of 2 mol/L aqueous sodium hydroxide solutionwas added to the mixture, and the resulting mixture was stirred at roomtemperature over-night. The reaction mixture was poured into water, andmade acidic with diluted hydrochloric acid. This mixture was extractedwith dichloromethane. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was distilled off and the residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by ethyl acetate) to obtain 120mg (0.349 mmol, Yield: 60.8%) of6-chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]-4-pyridazinol(Compound No. 827).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.25 (1H, br.d, J=6.3 Hz), 7.16 (1H, t,J=7.7 Hz), 6.98 (1H, d, J=7.7 Hz), 6.72 (1H, s), 2.85 (1H, dd, J=10.6,8.8 Hz), 2.22 (3H, s), 2.05-1.86 (2H, m). Melting point (° C.): 213-215.

EXAMPLE 25 6-Chloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]-4-pyridazinol(Compound No. 1109) (1) 6,7-Dihydro-1-benzofuran-4(5H)-one

In methanol (40 mL) was dissolved 11.2 g (0.100 mol) of1,3-cyclohexanedione, an aqueous solution (8 mL) containing 6.60 g(0.100 mol) of 85% potassium hydroxide was added dropwise to thesolution, and the resulting mixture was stirred at room temperature for30 minutes. This mixture was cooled in an ice bath, 21.6 g (0.110 mol)of 40% chloroacetaldehyde aqueous solution was added to the mixture withstirring and the resulting mixture was stirred at room temperatureovernight. To the reaction mixture was added dropwise 2 mol/Lhydrochloric acid aqueous solution, and the resulting mixture wasstirred at room temperature for 30 minutes and extracted with ether. Theorganic layer was successively washed with water and brine, and driedover anhydrous magnesium sulfate. The solvent was removed, and theobtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 8.63 g (0.0635 mol,Yield: 63.5%) of 6,7-dihydro-1-benzofuran-4(5H)-one.

(2) Methyl 4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate

In dry tetrahydrofuran (10 mL) was dissolved 3.00 g (22.1 mmol) of6,7-dihydro-1-benzofuran-4(5H)-one obtained in (1), and 48.5 mL (48.5mmol) of lithium bis(trimethylsilyl)amide (1.0 M tetrahydrofuransolution) was added dropwise to the solution under nitrogen atmosphereat −78° C. After stirring at −78° C. for 30 minutes, 1.87 mL (24.1 mmol)of methyl chlorocarbonate was added dropwise to the mixture, and thereaction mixture was warmed to room temperature and stirred for 10minutes. The reaction mixture was poured into water, and extracted withethyl acetate. The organic layer was successively washed with water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate, gradient) toobtain 3.93 g (20.3 mmol, Yield: 91.9%) of methyl4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate.

(3) Methyl 4-hydroxy-1-benzofuran-5-carboxylate

In 1,4-dioxane (100 mL) was dissolved 3.93 g (20.3 mmol) of methyl4-oxo-4,5,6,7-tetrahydro-1-benzofuran-5-carboxylate obtained in (2),5.51 g (24.3 mmol) of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone wasadded to the solution, and the resulting mixture was stirred at 120° C.for 3 hours. The reaction mixture was allowed to stand for cooling,insoluble materials were filtered off through Celite, and the filtratewas concentrated. The residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate, gradient) toobtain 2.04 g (10.6 mmol, Yield: 52.2%) of methyl4-hydroxy-1-benzofuran-5-carboxylate.

(4) Methyl 4-methoxy-1-benzofuran-5-carboxylate

To an acetonitrile (60 mL) solution containing 2.04 g (10.6 mmol) ofmethyl 4-hydroxy-1-benzofuran-5-carboxylate obtained in (3) were added2.53 g (18.3 mmol) of potassium carbonate, and then, 2.85 mL (45.8 mmol)of methyl iodide, and the resulting mixture was refluxed for 3 hours.After allowing to stand at room temperature overnight, the reactionmixture was poured into water, and extracted with ethyl acetate. Theorganic layer was successively washed with water and brine, and driedover anhydrous magnesium sulfate. The solvent was removed, and theobtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 2.01 g (9.76 mmol,Yield: 92.1%) of methyl 4-methoxy-1-benzofuran-5-carboxylate.

(5) (4-Methoxy-1-benzofuran-5-yl)methanol

To a dry tetrahydrofuran (20 mL) solution containing 1.01 g (4.90 mmol)of methyl 4-methoxy-1-benzofuran-5-carboxylate obtained in (4), 0.479 g(12.6 mmol) of lithium aluminum hydride was added little by little tothe mixture in an ice bath with stirring. The reaction mixture wasstirred in an ice bath for 2 hours, and ethyl acetate was added littleby little to the mixture. Subsequently, water (0.5 mL), 3N sodiumhydroxide (0.5 mL), and water (1.5 mL) were successively added to themixture and the resulting mixture was stirred for 30 minutes. Thismixture was filtered through Celite, and the filtrate was concentratedto obtain 0.89 g of a crude product of(4-methoxy-1-benzofuran-5-yl)methanol.

(6) 4-Methoxy-5-methyl-1-benzofuran

In dichloromethane (10 mL) was dissolved 0.65 g of a crude product of(4-methoxy-1-benzofuran-5-yl)methanol obtained in (5), 0.56 mL (4.03mmol) of triethylamine, and then, 0.31 mL (3.99 mmol) of methanesulfonylchloride were added dropwise to the solution in an ice bath withstirring, and the resulting mixture was stirred in an ice bath for 1hour. The reaction mixture was poured into water, and extracted withethyl acetate. The organic layer was successively washed with water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, dry dimethylsulfoxide (20 mL) was added to the obtainedresidue, and 0.276 g (7.30 mmol) of sodium borohydride was added littleby little. This mixture was stirred at room temperature for 1 hour, thenpoured into water, and extracted with ethyl acetate. The organic layerwas successively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05717, 3 plates were used, developed by hexane:ethylacetate=9:1) to obtain 0.284 g (1.75 mmol, Yield from methyl4-methoxy-1-benzofuran-5-carboxylate: 48.9%) of4-methoxy-5-methyl-1-benzofuran.

(7) 5-Methyl-1-benzofuran-4-ol

In dry N,N-dimethylformamide (11 mL) was suspended 268 mg (6.71 mmol) of60% sodium hydride, 0.51 mL (6.9 mmol) of ethanethiol was added dropwiseto the suspension under nitrogen atmosphere, and the resulting mixturewas stirred at room temperature for 10 minutes. To the mixture was addeda N,N-dimethylformamide (7 mL) solution containing 362 mg (2.23 mmol) of4-methoxy-5-methyl-1-benzofuran obtained in (6), and the resultingmixture was refluxed for 1 hour and 30 minutes. The reaction mixture wasallowed to stand for cooling, and 1 mol/L potassium hydroxide aqueoussolution and diethyl ether were added thereto. The aqueous layer waswashed with diethyl ether, and a pH thereof was adjusted by addingdiluted hydrochloric acid thereto to a pH 2. The mixture was extractedwith diethyl ether, the obtained organic layer was successively washedwith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by hexane:ethyl acetate=2:1) toobtain 276 mg (1.86 mmol, Yield: 83.4%) of 5-methyl-1-benzofuran-4-ol.

(8) 6-Chloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]pyridazine 1-oxide (StepB-2)

121 mg (0.818 mmol) of 5-methyl-1-benzofuran-4-ol obtained in (7) wasmixed with 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL), 101 mg(0.902 mmol) of potassium tert-butoxide was added to the mixture in anice bath, and the resulting mixture was stirred for 10 minutes. To themixture was added 134 mg (0.812 mmol) of 3,6-dichloropyridazine 1-oxide,and the resulting mixture was stirred at room temperature overnight. Thereaction mixture was poured into ice-cold water, and extracted withethyl acetate. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 3 plateswere used, developed by hexane:ethyl acetate=2:1 three times) to obtain199 mg of a crude product of6-chloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]pyridazine 1-oxide.

(9) 4,6-Dichloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]-pyridazine (StepB-3)

199 mg of a crude product of6-chloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]pyridazine 1-oxide obtainedin (8) and 3 mL of phosphorus oxychloride were mixed, and the mixturewas stirred at room temperature overnight. To the reaction mixture wereadded water and dichloromethane, and the resulting mixture was stirredfor 30 minutes. The mixture was separated, the organic layer wassuccessively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the residue waspurified by preparative thin-layer chromatography (available from MERCKCO., 1.05744, 3 plates were used, developed by hexane:ethyl acetate=2:1three times, subsequently available from MERCK CO., 1.05717, 2 plateswere used, developed by hexane:ethyl acetate=2:1 three times) to obtain120 mg (0.407 mmol, Yield from 4-hydroxy-5-methyl-1-benzofuran with 2Steps: 49.8%) of4,6-dichloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]pyridazine.

(10) 6-Chloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]-4-pyridazinol(Compound No. 1109, Step B-4)

120 mg (0.407 mmol) of4,6-dichloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]pyridazine obtained in(9) was mixed with 1,4-dioxane (3 mL) and dimethylsulfoxide (3 mL), 1.01mL (2.02 mmol) of 2 mol/L aqueous sodium hydroxide solution was added tothe mixture, and the resulting mixture was stirred at room temperatureovernight. The reaction mixture was poured into water, and made acidicwith diluted hydrochloric acid. This mixture was extracted withdichloromethane. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 2 plateswere used, developed by ethyl acetate) to obtain 70.0 mg (0.253 mmol,Yield: 62.2%) of6-chloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]-4-pyridazinol (Compound No.1109).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.65 (1H, d, J=2.2 Hz), 7.32 (1H, d,J=8.8 Hz), 7.18 (1H, d, J=8.8 Hz), 6.73 (1H, s), 6.60 (1H, dd, J=2.2,0.7 Hz), 2.23 (3H, s). Melting point (° C.): 222-225.

EXAMPLE 26 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyltrifluoromethanesulfonate (Compound No. 2081, Step I-1)

In methylene chloride (2 mL) was dissolved 50.3 mg (0.191 mmol) of6-chloro-3-(2-cyclopropylphenoxy)-4-pyridazinol (Compound No. 139)obtained in Example 6, 0.027 mL (0.19 mmol) of triethylamine was addeddropwise to the solution, then, 0.031 mL (0.19 mmol) oftrifluoromethanesulfonic acid anhydride was added dropwise to the same,and the resulting mixture was stirred at room temperature for 30minutes. The reaction mixture was purified as such by preparativethin-layer chromatography (available from MERCK Co., 1.05744, 2 plateswere used, developed by ethyl acetate:hexane=2:1) to obtain 64.7 mg(0.164 mmol, Yield: 85.8%) of6-chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyltrifluoromethanesulfonate (Compound No. 2081).

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.51 (1H, s), 7.26-7.19 (2H, m),7.14-7.05 (2H, m), 1.89-1.81 (1H, m), 0.85-0.62 (4H, m). Melting point(° C.): 54-61.

EXAMPLE 27 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl4-methylbenzene sulfonate (Compound No. 2225, Step I-1)

In acetonitrile (3 mL) was dissolved 53.4 mg (0.203 mmol) of6-chloro-3-(2-cyclopropylphenoxy)-4-pyridazinol (Compound No. 139)obtained in Example 6, 23.1 mg (0.206 mmol) of1,4-diazabicyclo[2,2,2]octane was added to the solution, then, 39.2 mg(0.205 mmol) of 4-methylbenzene sulfonyl chloride was added to the same,and the resulting mixture was stirred at room temperature for 1 hour and30 minutes. The reaction mixture was poured into water, and extractedwith ethyl acetate. The organic layer was successively washed with waterand brine, and dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the obtained residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, ethylacetate:hexane=2:1) to obtain 68.8 mg (0.165 mmol, Yield: 81.3%) of6-chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl 4-methylbenzenesulfonate (Compound No. 2225).

H¹-NMR (200 MHz, CDCl₃) δ ppm: 7.87 (2H, d, J=8.1 Hz), 7.58 (1H, s),7.36 (2H, d, J=8.1 Hz), 7.26-7.11 (2H, m), 6.97-6.93 (1H, m), 6.74-6.70(1H, m), 2.45 (3H, s), 1.67-1.59 (1H, m), 0.71-0.56 (4H, m). Appearance:oily product.

EXAMPLE 282-[(6-Chloro-4-{[(4-methylphenyl)sulfonyl]oxy}-3-pyridazinyl)oxy]phenyl4-methylbenzene sulfonate (Compound No. 2233, Step I-1)

0.60 g (2.5 mmol) of 6-chloro-3-(2-hydroxyphenoxy)-4-pyridazinol(Compound No. 384) obtained in Example 10, 1.06 g (5.5 mmol) of4-methylbenzene sulfonyl chloride, 0.56 g (5.0 mmol) of1,4-diazabicyclo[2,2,2]octane and acetonitrile (30 mL) were mixed, andthe mixture was stirred under reflux for 3 hours, and at roomtemperature for 4 days. Acetonitrile was removed by distillation, waterwas added to the residue, and the mixture was extracted with ethylacetate. The organic layers were combined, washed with water, and driedover anhydrous sodium sulfate. The solvent was removed, and the residuewas washed with a mixed solvent of hexane-ethyl acetate (3:1) to obtain1.0 g (1.8 mmol, Yield: 72%) of2-[(6-chloro-4-{[(4-methylphenyl)sulfonyl]oxy}-3-pyridazinyl)oxy]phenyl4-methylbenzene sulfonate (Compound No. 2233).

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.98-6.65 (13H, m), 2.40 (3H, s), 2.36(3H, s). Melting point (° C.): 125.5-126.5.

EXAMPLE 29 6-Chloro-5-methyl-3-(2-methylphenoxy)-4-pyridazinol (CompoundNo. 2372) (1) 3-Chloro-4-methyl-2,5-furandione and3-chloro-4-(chloromethyl)-2,5-furandione

224 g (2.00 mol) of 3-methyl-2,5-furandione and 11.2 g (0.415 mol) ofiron chloride (III) hexahydrate were mixed, and the mixture was heatedto 140° C., and 346 g (4.88 mol) of a chlorine gas was passed throughthe mixture with stirring over 7 hours and 30 minutes. Thereafter, themixture was heated at 175° C. for 3 hours and 30 minutes. The reactionmixture was evaporated under reduced pressure (5 mmHg) to collectfractions of 80° C. to 85° C. Thus, 223.5 g of a crude product(containing 3-chloro-4-methyl-2,5-furandione and3-chloro-4-(chloromethyl)-2,5-furandione) was obtained.

(2) 4-Chloro-5-methyl-1,2-dihydro-3,6-pyridazinedione and4-chloro-5-(chloromethyl)-1,2-dihydro-3,6-pyridazinedione

147 g of a material (containing 3-chloro-4-methyl-2,5-furandione and3-chloro-4-(chloromethyl)-2,5-furandione) obtained in (1) was mixed with400 mL of water, and the mixture was refluxed to make a solution. To thesolution heated at reflux was added dropwise an aqueous solutioncontaining 116 g (1.10 mol) of hydrazine dihydrochloride (the hydrazinedihydrochloride was dissolved in 400 mL of water) over 40 minutes.Thereafter, the mixture was refluxed for 1 hour and 30 minutes, and thenallowed to stand for cooling. Precipitated crystals were collected byfiltration, washed with hot water, and then, with ethyl acetate, toobtain 81.8 g of 4-chloro-5-methyl-1,2-dihydro-3,6-pyridazinedione (m.p.305-310° C.). On the other hand, the filtrate was extracted with ethylacetate, the organic layers were combined, washed with water, and driedover anhydrous sodium sulfate. The solvent was removed, and a mixturecontaining 8.06 g of4-chloro-5-(chloromethyl)-1,2-dihydro-3,6-pyridazinedione was obtainedas a residue.

(3) 3,4,6-Trichloro-5-methylpyridazine

24.1 g (0.150 mol) of 4-chloro-5-methyl-1,2-dihydro-3,6-pyridazinedioneobtained in (2) was mixed with 250 mL (2.76 mol) of phosphorusoxychloride, and the mixture was refluxed for 1 hour and 40 minutes.Excess phosphorus oxychloride was removed from the reaction mixture bydistillation, and the residue was mixed with ice water. Crystals werecollected by filtration, and extracted with ethyl acetate. The organiclayer was washed with water, and the solvent was removed. The obtainedresidue was distilled under reduced pressure (0.7 mmHg) and fractions at105° C. to 110° C. were collected to obtain 25.1 g (0.127 mol, Yield:84.7%, m.p. 67.5-70° C.) of 3,4,6-trichloro-5-methylpyridazine.

(4) 3,6-Dichloro-4-methoxy-5-methylpyridazine

7.90 g (40.1 mmol) of 3,4,6-trichloro-5-methylpyridazine obtained in (3)was mixed with methanol (100 mL), a methanol solution (50 mL) containing0.92 g (40 mmol) of sodium was added dropwise to the mixture in an icebath, thereafter in an ice bath, the mixture was stirred for 1 hour, andthen, for 15 minutes under reflux. In an ice bath, 0.20 g (8.7 mmol) ofsodium was additionally added to the mixture, and the resulting mixturewas further refluxed for 15 minutes. The reaction mixture was allowed tostand for cooling, and methanol was distilled off. The residue was mixedwith ice water and extracted with ethyl acetate. The organic layers werecombined, washed with water, and the solvent was removed. The obtainedresidue was purified by silica gel column chromatography (Wako gelC-100, eluted with hexane:ethyl acetate=5:1) to obtain 5.1 g of a crudeproduct. This product was distilled under reduced pressure (0.07 mmHg)and fractions at 125° C. were collected to obtain 4.50 g (23.3 mmol,Yield: 58.1%) of 3,6-dichloro-4-methoxy-5-methylpyridazine.

(5) Mixture of 3-chloro-5-methoxy-4-methyl-6-(2-methylphenoxy)pyridazineand 3-chloro-4-methoxy-5-methyl-6-(2-methylphenoxy)pyridazine (Step D-1)

To 30.8 g (285 mmol) of 2-methylphenol was gradually added 1.66 g (38.0mmol) of 55% sodium hydride with stirring. After stirring at roomtemperature for 20 minutes, the mixture was heated to 90° C. todisappear a solid of sodium hydride. This mixture was cooled to 50° C.,3.69 g (19.1 mmol) of 3,6-dichloro-4-methoxy-5-methylpyridazine obtainedin (4) was added thereto, and the resulting mixture was stirred at 110°C. for 3 hours and 30 minutes. The reaction mixture was allowed to standfor cooling, water was added thereto, and then, the mixture wasextracted with ethyl acetate. The organic layer was washed with 20%aqueous sodium hydroxide solution, and the solvent was removed. Theobtained residue was purified by silica gel column chromatography toobtain 1.38 g (5.21 mmol, Yield: 27.3%) of a mixture of3-chloro-5-methoxy-4-methyl-6-(2-methylphenoxy)pyridazine and3-chloro-4-methoxy-5-methyl-6-(2-methylphenoxy)pyridazine.

(6) 6-Chloro-5-methyl-3-(2-methylphenoxy)-4-pyridazinol (Compound No.2372, Step D-2)

1.38 g (5.21 mmol) of a mixture of3-chloro-5-methoxy-4-methyl-6-(2-methylphenoxy)pyridazine and3-chloro-4-methoxy-5-methyl-6-(2-methylphenoxy)pyridazine obtained in(5) was mixed with 1,4-dioxane (8 mL), an aqueous solution (using 13 mLof water) containing 0.282 g (6.78 mmol) of 96% sodium hydroxide wasadded to the mixture, and the resulting mixture was stirred at 110° C.for 4.5 hours. Water was poured into the reaction mixture, and themixture was extracted with ethyl acetate. The aqueous layer was madeacidic with hydrochloric acid, and precipitated crystals were collectedby filtration to obtain 0.249 g (0.992 mmol, Yield: 19.0%, m.p. 209-213°C.) of 6-chloro-5-methyl-3-(2-methylphenoxy)-4-pyridazinol (Compound No.2372).

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.50-6.95 (4H, m), 2.28 (3H, m), 2.11(3H, m). Melting point (° C.): 209-213.

Incidentally, crystals precipitated from the filtrate were collected byfiltration to obtain 0.187 g (0.745 mmol, Yield: 14.3%) of3-chloro-5-methyl-6-(2-methylphenoxy)-4-pyridazinol. On the other hand,the organic layer was dried over anhydrous sodium sulfate, and thesolvent was removed to recover 0.57 g (Recovery: 41%) of the startingmaterial.

EXAMPLE 30 6-Chloro-5-(methoxymethyl)-3-(2-methylphenoxy)-4-pyridazinol(Compound No. 2378) (1) 3,4,6-Trichloro-5-(chloromethyl)pyridazine

7.8 g of a mixture containing4-chloro-5-(chloromethyl)-1,2-dihydro-3,6-pyridazinedione obtained inExample 29 was added 50 mL of phosphorus oxychloride, and the mixturewas refluxed for 1 hour. Excess phosphorus oxychloride was distilled offfrom the reaction mixture, and the residue was mixed with ice water. Themixture was extracted with ethyl acetate, the organic layers werecombined, washed with water, and dried over anhydrous sodium sulfate.The solvent was removed, and the obtained residue was purified by silicagel column chromatography (available from Merck Co., 9385, eluted withhexane:ethyl acetate=10:1) to obtain 3.63 g (15.6 mmol, m.p. 102-104°C.) of 3,4,6-trichloro-5-(chloromethyl)pyridazine.

(2) 3,6-Dichloro-4-methoxy-5-(methoxymethyl)pyridazine

In methanol (50 ml) was added 2.32 g (10.0 mmol) of3,4,6-trichloro-5-(chloromethyl)pyridazine obtained in (1) and themixture was heated to make a solution. Then, the solution was cooled to−60° C. and a methanol solution of sodium methoxide (prepared from 0.23g of sodium and 5 mL of methanol, 10.0 mmol) was added dropwise to thesolution. The solution was stirred at −10° C. for 2 hours and 30minutes, and a methanol solution of sodium methoxide (prepared from 0.23g of sodium and 5 mL of methanol, 10.0 mmol) was further added dropwiseto the solution. After stirring for 2 hours at −10° C., and the mixturewas allowed to stand at room temperature overnight. The reaction mixturewas concentrated, and the residue was purified by silica gel columnchromatography (available from Merck Co., 9385, eluted with hexane:ethylacetate=5:1) to obtain 1.85 g (8.30 mmol, Yield: 83.0%, m.p. 28-32° C.)of 3,6-dichloro-4-methoxy-5-(methoxymethyl)pyridazine.

(3)3-Chloro-5-methoxy-4-(methoxymethyl)-6-(2-methylphenoxy)pyridazine(StepD-1)

432 mg (4.00 mmol) of 2-methylphenol, methanol (20 mL) and 92 mg (4.0mmol) of sodium were mixed, and the mixture was stirred at roomtemperature until sodium was disappeared. Methanol in the mixture wasdistilled off, 50 mL of toluene was added to the residue and the mixturewas refluxed. The mixture was cooled in an ice bath, a toluene solution(10 mL) containing 892 mg (4.00 mmol) of3,6-dichloro-4-methoxy-5-(methoxymethyl)pyridazine obtained in (2) wasadded dropwise to the mixture, and the resulting mixture was refluxedfor 3 hours. The reaction mixture was allowed to stand at roomtemperature overnight, washed with water, and then with brine, and driedover anhydrous sodium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (First time; availablefrom Merck Co., 9385, eluted with hexane:ethyl acetate=5:1. Second time;available from Merck Co., 9385, eluted with hexane:ethyl acetate=8:1) toobtain 0.487 g (1.65 mmol, Yield: 41.3%) of3-chloro-5-methoxy-4-(methoxymethyl)-6-(2-methylphenoxy)pyridazine and0.266 g (0.902 mmol, Yield: 22.6%) of3-chloro-4-methoxy-5-(methoxymethyl)-6-(2-methylphenoxy)pyridazine.

(4) 6-Chloro-5-(methoxymethyl)-3-(2-methylphenoxy)-4-pyridazinol(Compound No. 2378, Step D-2)

0.354 g (1.20 mmol) of3-chloro-5-methoxy-4-(methoxymethyl)-6-(2-methylphenoxy)pyridazineobtained in (3), 1,4-dioxane (2 mL), 62 mg (1.49 mmol) of 96% sodiumhydroxide and water (8 mL) were mixed, and the mixture was stirred atroom temperature for 2 days, and further for 3 hours under reflux.Hydrochloric acid was added to the reaction mixture to make a pH 1, andthen, the mixture was extracted with ethyl acetate. The organic layerswere combined, washed with water, and dried over anhydrous sodiumsulfate. The solvent was removed to obtain 0.336 g (1.20 mmol, Yield:100%) of 6-chloro-5-(methoxymethyl)-3-(2-methylphenoxy)-4-pyridazinol(Compound No. 2378).

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 8.92 (1H, brs), 7.45-6.80 (4H, m), 4.39(2H, s), 3.25 (3H, s), 2.25 (3H, s). Melting point (° C.): 123-126.

EXAMPLE 31 Ethyl6-(2-tert-butylphenoxy)-3-chloro-5-hydroxy-4-pyridazinecarboxylate(Compound No. 2386) (1)3-(2-Tert-butylphenoxy)-6-chloro-4-methoxypyridazine

5.87 g (39.1 mmol) of 2-tert-butylphenol, dimethylsulfoxide (80 mL) and4.38 g (39.0 mmol) of potassium t-butoxide were mixed, and the mixturewas stirred at room temperature for 20 minutes. To the mixture was addeda dimethylsulfoxide solution (60 mL) containing 6.92 g (38.7 mmol) of3,6-dichloro-4-methoxypyridazine, and the resulting mixture was stirredat room temperature for 40 minutes, and at 80° C. for 45 minutes. Thereaction mixture was poured into a saturated aqueous ammonium chloridesolution, and extracted with ethyl acetate. The organic layers werecombined, washed with water, and then, with brine, and dried overanhydrous sodium sulfate. The solvent was removed, and the residue waspurified by silica gel column chromatography (available from Merck Co.,9385, hexane:ethyl acetate, gradient) to obtain 2.66 g (9.09 mmol,Yield: 23.5%) of 3-(2-tert-butylphenoxy)-6-chloro-4-methoxypyridazineand 1.82 g (6.22 mmol, Yield: 16.1%) of6-(2-tert-butylphenoxy)-3-chloro-4-methoxypyridazine.

(2) Ethyl6-(2-tert-butylphenoxy)-3-chloro-5-methoxy-4-pyridazinecarboxylate (StepG-1)

In dry tetrahydrofuran (26 mL) was dissolved 783 mg (2.68 mmol) of3-(2-tert-butylphenoxy)-6-chloro-4-methoxypyridazine obtained in (1).The solution was cooled to −78° C., 1.20 mL (2.80 mmol) of a n-butyllithium-hexane solution (2.33M) was added to the solution and theresulting mixture was stirred for 20 minutes. To the mixture was added0.330 mL (3.45 mmol) of ethyl chlorocarbonate, and the resulting mixturewas stirred at the same temperature for 30 minutes. The reaction mixturewas poured into a saturated aqueous ammonium chloride solution, andextracted with ether. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (eluted with hexane:ethylacetate=5:1) to obtain 603 mg (1.65 mmol, Yield: 61.6%) of ethyl6-(2-tert-butylphenoxy)-3-chloro-5-methoxy-4-pyridazinecarboxylate.

(3) Eethyl6-(2-tert-butylphenoxy)-3-chloro-5-hydroxy-4-pyridazinecarboxylate(Compound No. 2386, Step G-2)

419 mg (1.15 mmol) of ethyl6-(2-tert-butylphenoxy)-3-chloro-5-methoxy-4-pyridazinecarboxylateobtained in (2), 1,4-dioxane, 1 mol/L aqueous sodium hydroxide solution(2.0 mL, 2.0 mmol) and dimethylsulfoxide (2.0 mL) were mixed, and themixture was stirred at room temperature for 2 hours and 30 minutes, andat 80° C. for 4 hours and 30 minutes. After allowing to stand forcooling, the reaction mixture was made acidic with hydrochloric acid,and extracted with dichloromethane. The organic layers were combined,washed with brine, and dried over anhydrous sodium sulfate. The solventwas removed, and the residue was purified by silica gel columnchromatography to obtain 337 mg (0.960 mmol, Yield: 83.5%) of ethyl6-(2-tert-butylphenoxy)-3-chloro-5-hydroxy-4-pyridazinecarboxylate(Compound No. 2386). Appearance: amorphous.

EXAMPLE 32 3,6-Bis(2-methylphenoxy)-4-pyridazinol (Compound No. 2395)(1) 3-chloro-5-methoxy-4,6-bis(2-methylphenoxy)pyridazine (Step D-1)

In toluene (100 mL) was dissolved 5.32 g (49.3 mmol) of 2-methylphenol,and 1.13 g (49.1 mmol) of sodium, and then, 5.80 g (27.2 mmol) of3,4,6-trichloro-5-methoxypyridazine were added to the solution and theresulting mixture was stirred for 4 hours under reflux. The reactionmixture was poured into ice-cold water, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, and dried over anhydrous sodium sulfate. The solventwas removed, and the residue was purified by silica gel columnchromatography (hexane:ethyl acetate, gradient) and recrystallized fromisopropyl ether to obtain 3.0 g (8.4 mmol, Yield: 31%) of3-chloro-5-methoxy-4,6-bis(2-methylphenoxy)pyridazine.

(2) 6-Chloro-3,5-bis(2-methylphenoxy)-4-pyridazinol (Compound No. 2395,Step D-2)

0.72 g (2.0 mmol) of3-chloro-5-methoxy-4,6-bis(2-methylphenoxy)pyridazine obtained in (1)was added to a mixture comprising 0.60 mL (4.7 mmol) of trimethylsilylchloride, 0.60 g (4.0 mmol) of sodium iodide and acetonitrile (15ml),and the resulting mixture was stirred overnight. The reaction mixturewas poured into ice-cold water, and extracted with methylene chloride.The organic layers were combined, washed successively with water andbrine, and dried over anhydrous sodium sulfate. The solvent was removed,and the residue was purified by silica gel column chromatography(chloroform: methanol, gradient) to obtain 0.45 g (1.3 mmol, Yield: 65%)of 6-chloro-3,5-(2-methylphenoxy)-4-pyridazinol (Compound No. 2395).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.32-7.05 (7H, m), 6.91 (1H, br.d, J=7.3Hz), 2.29 (3H, s), 2.19 (3H, s). Melting point (° C.): 110-115.

EXAMPLE 333-(2-tert-Butylphenoxy)-6-chloro-5-(trimethylsilyl)-4-pyridazinol(Compound No. 2405) (1)3-(2-tert-Butylphenoxy)-6-chloro-4-methoxy-5-(trimethylsilyl)pyridazine(StepG-1)

In dry tetrahydrofuran (15 mL) was dissolved 498 mg (1.70 mmol) of3-(2-tert-butylphenoxy)-6-chloro-4-methoxypyridazine obtained in Example31 (1), the solution was cooled to −78° C., 1.10 mL (1.87 mmol) of an-butyl lithium-hexane solution (1.70M) was added to the solution andthe resulting mixture was stirred for 20 minutes. To the mixture wasadded 0.370 mL (2.91 mmol) of trimethylsilyl chloride, and the resultingmixture was stirred at the same temperature for 10 minutes. The reactionmixture was poured into a saturated aqueous ammonium chloride solution,extracted with ether. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography to obtain 596 mg (1.63 mmol, Yield:95.9%) of3-(2-tert-butylphenoxy)-6-chloro-4-methoxy-5-(trimethylsilyl)pyridazine.

(2) 3-(2-tert-Butylphenoxy)-6-chloro-5-(trimethylsilyl)-4-pyridazinol(Compound No. 2405, Step G-2)

0.17 g (1.1 mmol) of sodium iodide, 0.14 mL (1.1 mmol) of trimethylsilylchloride and acetonitrile (3.5 mL) were mixed, and to the mixture wasadded with stirring 340 mg (0.932 mmol) of3-(2-tert-butylphenoxy)-6-chloro-4-methoxy-5-(trimethylsilyl)pyridazineobtained in (1), and the resulting mixture was stirred at roomtemperature for 1 hour and 35 minutes. The reaction mixture was pouredinto a saturated aqueous sodium sulfite solution, and ice-cold dilutedhydrochloric acid was added to the mixture. The mixture was extractedwith ethyl acetate, the organic layers were combined and washed withbrine. The solvent was removed, and the residue was purified by silicagel column chromatography to obtain 275 mg (0.783 mmol, Yield: 84.0%) of3-(2-tert-butylphenoxy)-6-chloro-5-(trimethylsilyl)-4-pyridazinol(Compound No. 2405).

¹H-NMR (90 MHz, CDCl₃) δ ppm: 10.12 (1H, brs), 7.39-6.75 (4H, m), 1.24(9H, s), 0.31 (9H, s). Melting point (° C.): 160-163.

EXAMPLE 34 6-Bromo-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 2411)(1) 5-chloro-6-(2-methylphenoxy)-3-pyridazinol (Step P-1)

A mixture comprising 578 mg (2.27 mmol) of4,6-dichloro-3-(2-methylphenoxy)pyridazine obtained in Example 1 (2),acetic acid (10 mL) and 0.45 g (4.6 mmol) of potassium acetate wasrefluxed for 5 hours. The reaction mixture was allowed to stand forcooling, and after adding 50 mL of water, the mixture was extracted withethyl acetate. The organic layers were combined, and washed successivelywith water and brine. After drying over anhydrous sodium sulfate, thesolvent was removed to obtain 461 mg (1.95 mmol, Yield: 85.9%) of5-chloro-6-(2-methylphenoxy)-3-pyridazinol.

(2) 4,6-Dibromo-3-(2-methylphenoxy)pyridazine (Step P-2)

151 mg (0.637 mmol) of 5-chloro-6-(2-methylphenoxy)-3-pyridazinolobtained in (1), chloroform(3 mL) and 913 mg (3.18 mmol) of phosphorusoxybromide were mixed, and the mixture was refluxed for 5 hours. Thereaction mixture was allowed to stand for cooling, water anddichloromethane were added to the mixture and the resulting mixture wasstirred at room temperature for 1 hour. The mixture was extracted withdichloromethane. The organic layers were combined, and washedsuccessively with water and brine. After drying over anhydrous sodiumsulfate, the solvent was removed. The obtained residue was purified bysilica gel column chromatography to obtain 176 mg (0.512 mmol, Yield:80.4%) of 4,6-dibromo-3-(2-methylphenoxy)pyridazine.

(3) 6-Bromo-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 2411, StepP-3)

In dimethylsulfoxide (3 mL) was dissolved 114 mg (0.331 mmol) of4,6-dibromo-3-(2-methylphenoxy)pyridazine obtained in (2), 0.80 mL (1.6mmol) of 2 mol/L aqueous sodium hydroxide solution was added to thesolution, and the resulting mixture was stirred at room temperature for3 hours. Water was added to the reaction mixture, and the resultingmixture was washed with ethyl acetate. The aqueous layer was made acidicwith 4 mol/L hydrochloric acid, and extracted with ethyl acetate. Theorganic layers were combined, washed with brine and dried over anhydroussodium sulfate. The solvent was removed, and the residue was washed witha mixed solvent of ethyl acetate-ether to obtain 56.0 mg (0.199 mmol,Yield: 60.1%) of 6-bromo-3-(2-methylphenoxy)-4-pyridazinol (Compound No.2411).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.35-7.05 (4H, m), 6.82 (1H, brs), 2.10(3H, s). Melting point (° C.): 197-198.

EXAMPLE 35 6-Cyclopropyl-3-(2-methylphenoxy)-4-pyridazinol (Compound No.2423) (1) 6-Cyclopropyl-4-methoxy-3-(2-methylphenoxy)pyridazine (StepL-1)

To a tetrahydrofuran solution (2.94 mL) containing of9-borabicyclo[3.3.1]nonane (0.5 mol/l, 1.47 mmol) was added 87.5 mg(0.735 mmol) of propargyl bromide, and the resulting mixture wasrefluxed for 2 hours. The reaction mixture was cooled to roomtemperature, 0.74 mL (2.2 mmol) of 3 mol/L aqueous sodium hydroxidesolution was added to the mixture, and the resulting mixture was stirredat room temperature for 70 minutes. To the mixture were successivelyadded 168 mg (0.669 mmol) of6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2(1) and 38.7 mg (0.00334 mmol) oftetrakis(triphenylphosphine)-palladium, and the resulting mixture wasrefluxed overnight. The reaction mixture was allowed to stand forcooling, water was added to the mixture, and the resulting mixture wasextracted with ethyl acetate. The organic layers were combined, andwashed successively with water and brine. After drying over anhydroussodium sulfate, the solvent was removed. The obtained residue waspurified by silica gel column chromatography to obtain 121 mg (0.473mmol, Yield: 70.1%) of6-cyclopropyl-4-methoxy-3-(2-methylphenoxy)pyridazine.

(2) 6-Cyclopropyl-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 2423,Step L-2)

In dimethylsulfoxide (2 mL) was dissolved 45.6 mg (0.479 mmol) of2-hydroxypyridine, 53.8 mg (0.480 mmol) of potassium tert-butoxide wasadded the solution at room temperature, and the resulting mixture wasstirred at room temperature for 10 minutes. To the mixture was added adimethylsulfoxide (1 mL) solution containing 112 mg (0.438 mmol) of6-cyclopropyl-4-methoxy-3-(2-methylphenoxy)-pyridazine obtained in (1),and the resulting mixture was stirred at 60° C. for 5 hours, and at 80°C. for 15 hours. Moreover, 45.6 mg (0.479 mmol) of 2-hydroxypyridine andthen 53.8 mg (0.480 mmol) of potassium tert-butoxide were additionallyadded to the mixture, and the resulting mixture was stirred at 80° C.for 4 hours and 30 minutes. The reaction mixture was allowed to standfor cooling, water was added to the mixture, and and the resultingmixture was washed with ethyl acetate. The aqueous layer was made acidicwith 4 mol/L hydrochloric acid, and extracted with ethyl acetate. Theorganic layers were combined, and washed successively with water andbrine. After drying over anhydrous sodium sulfate, the solvent wasremoved. The obtained residue was purified by preparative thin-layerchromatography (available from Merck Co., 1.05744, developed by ethylacetate) to obtain 28.6 mg (0.118 mmol, Yield: 26.9%) of6-cyclopropyl-3-(2-methylphenoxy)-4-pyridazinol (Compound No. 2423).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.30-7.01 (4H, m), 6.19 (1H, s),1.98-1.82 (1H, m), 1.23-1.12 (2H, m), 0.99-0.88 (2H, m). Melting point(° C.): 214-215.

EXAMPLE 36 3-(2-Methylphenoxy)-6-vinyl-4-pyridazinol (Compound No. 2436)(1) 4-Methoxy-3-(2-methylphenoxy)-6-vinylpyridazine (Step L-1)

In toluene (2 mL) was dissolved 123 mg (0.490 mmol) of6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2(1), 246 mg (0.776 mmol) of tributyl-(vinyl)tin, and then, 119 mg (0.103mmol) of tetrakis(triphenylphosphine)palladium were successively addedto the solution at room temperature, and the resulting mixture wasrefluxed for 3 hours. The reaction mixture was allowed to stand forcooling, ethyl acetate (5 mL), water (3 mL) and sodium fluoride wereadded to the mixture, and the resulting mixture was stirred for 30minutes and allowed to stand at at room temperature overnight. Themixture was filtered through Celite, ethyl acetate was added to thefiltrate, then the organic layer was separated and washed with brine.After drying over anhydrous sodium sulfate, the solvent was removed. Theobtained residue was purified by silica gel column chromatography(eluted with hexane:ethyl acetate=1:2) to obtain 105 mg (0.434 mmol,Yield: 88.6%) of 4-methoxy-3-(2-methylphenoxy)-6-vinylpyridazine.

(2) 3-(2-Methylphenoxy)-6-vinyl-4-pyridazinol (Compound No. 2436, StepL-2)

In dimethylsulfoxide (1 mL) was dissolved 33.7 mg (0.354 mmol) of2-hydroxypyridine, 39.7 mg (0.354 mmol) of potassium tert-butoxide wasadded to the solution at room temperature, and the resulting mixture wasstirred at room temperature for 10 minutes. To the mixture was added adimethylsulfoxide (1 mL) solution containing 85.8 mg (0.354 mmol) of4-methoxy-3-(2-methylphenoxy)-6-vinylpyridazine obtained in (1), and theresulting mixture was stirred at room temperature overnight and at 50°C. for 4 hours and 30 minutes. The reaction mixture was allowed to standfor cooling, water was added thereto, and the resulting mixture waswashed with ethyl acetate. The aqueous layer was made acidic with 4mol/L hydrochloric acid, and extracted with ethyl acetate. The organiclayers were combined, dried over anhydrous sodium sulfate, and thesolvent was removed. The obtained residue was purified by silica gelcolumn chromatography (eluted with hexane:ethyl acetate=1:4) to obtain51.7 mg (0.227 mmol, Yield: 64.1%) of3-(2-methylphenoxy)-6-vinyl-4-pyridazinol (Compound No. 2436).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.35-7.03 (4H, m), 6.56-6.43 (2H, m),6.16 (1H, d, J=17.9 Hz), 6.16 (1H, d, J=11.4 Hz), 2.11 (3H, s). Meltingpoint (° C.): 195-197.

EXAMPLE 37 3-(2-Methylphenoxy)-6-(1-propenyl)-4-pyridazinol (CompoundNo. 2442) (1) 6-Allyl-4-methoxy-3-(2-methylphenoxy)pyridazine (Step L-1)

In toluene (4 mL) was dissolved 200 mg (0.797 mmol) of6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2(1), 305 mg (0.921 mmol) of allyl-(tributyl)tin, and then, 96.8 mg(0.0838 mmol) of tetrakis-(triphenylphosphine)palladium weresuccessively added to the solution at room temperature, and theresulting mixture was refluxed for 3 hours and 20 minutes. The reactionmixture was allowed to stand at room temperature overnight, and then,ethyl acetate, water and sodium fluoride were added to the mixture andthe resulting mixture was stirred for 2 hours. The mixture was filteredthrough Celite, ethyl acetate was added to the filtrate, then theorganic layer was separated, and washed successively with water andbrine. After drying over anhydrous sodium sulfate, the solvent wasremoved. The obtained residue was purified by silica gel columnchromatography (hexane:ethyl acetate, gradient) to obtain 62.1 mg (0.243mmol, Yield: 30.5%) of 6-allyl-4-methoxy-3-(2-methylphenoxy)pyridazine.

(2) 3-(2-Methylphenoxy)-6-(1-propenyl)-4-pyridazinol (Compound No. 2442,Step L-2)

In dimethylsulfoxide (2 mL) was dissolved 25.3 mg (0.267 mmol) of2-hydroxypyridine, 29.9 mg (0.267 mmol) of potassium tert-butoxide wasadded to the solution at room temperature, and the resulting mixture wasstirred at room temperature for 10 minutes. To the mixture was added adimethylsulfoxide (3 mL) solution containing 62.1 mg (0.243 mmol) of6-allyl-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in (1), and theresulting mixture was stirred at 100° C. for 8 hours and at 130° C. for5 hours and 30 minutes. Moreover, 25.3 mg (0.267 mmol) of2-hydroxypyridine, and then, 29.9 mg (0.267 mmol) of potassiumtert-butoxide were additionally added to the mixture, and the resultingmixture was stirred at 130° C. for 5 hours. The reaction mixture wasallowed to stand for cooling, and after adding water, the mixture waswashed with ethyl acetate. The aqueous layer was made acidic with 4mol/L hydrochloric acid, and extracted with ethyl acetate. The organiclayers were combined, dried over anhydrous sodium sulfate, and thesolvent was removed. The obtained residue was purified by preparativethin-layer chromatography (available from Merck Co., 1.05744, 3 plateswere used, developed by ethyl acetate) to obtain 21.3 mg (0.0880 mmol,Yield: 36.2%) of 3-(2-methylphenoxy)-6-(1-propenyl)-4-pyridazinol(Compound No. 2442).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.32-7.03 (4H, m), 6.75-6.60 (1H, m),6.44 (1H, s), 6.22-6.10 (1H, m), 2.10 (3H s), 1.86 (3H, br.d, J=6.6 Hz).Melting point (° C.): 208-210.

EXAMPLE 38 6-(2,6-Dimethylphenoxy)-5-hydroxy-3-pyridazinecarbonitrile(Compound No. 2453) (1)6-Chloro-3-(2,6-dimethylphenoxy)-4-methoxypyridazine 1-oxide (Step K-1)

3.42 g (12.9 mmol) of6-chloro-3-(2,6-dimethylphenoxy)-4-methoxypyridazine, dichloromethane(110 mL) and 3.34 g (15.4 mmol) of 80% m-chloroperbenzoic acid weremixed, and the mixture was stirred at at room temperature for 16 days.The reaction mixture was poured into ice-cold saturated aqueous sodiumsulfite solution, and extracted with dichloromethane. The organic layerswere combined, washed successively with a saturated aqueous sodiumhydrogen carbonate solution, water and brine, and dried over anhydroussodium sulfate. The solvent was removed, and the residue was purified bysilica gel column chromatography to obtain 2.06 g (7.33 mmol, Yield:56.8%) of 6-chloro-3-(2,6-dimethylphenoxy)-4-methoxypyridazine 1-oxide.

(2) 3-(2,6-Dimethylphenoxy)-4-methoxypyridazine 1-oxide (Step K-2)

6.00 g (21.4 mmol) of6-chloro-3-(2,6-dimethylphenoxy)-4-methoxypyridazine 1-oxide obtained in(1), methanol (200 mL), 3.0 mL of triethylamine, acetone (5 mL) and 0.5g of 5% palladium carbon were mixed, and the mixture was shaked by usinga Parr reducing device under a hydrogen pressure of 3.5 atm for 2 hours.The reaction mixture was filtered, and the filtrate was concentrated.Water was added to the residue, and the mixture was extracted withchloroform. The organic layers were combined, washed with brine, anddried over anhydrous sodium sulfate. The solvent was removed, and theresidue was crystallized from an ether-dichloromethane mixed solvent toobtain 4.32 g (17.6 mmol, Yield: 82.2%) of3-(2,6-dimethylphenoxy)-4-methoxypyridazine 1-oxide.

(3) 6-(2,6-Dimethylphenoxy)-5-methoxy-3-pyridazinecarbonitrile (StepM-1)

In dry N,N-dimethylformamide (15 mL) was dissolved 0.720 g (2.92 mmol)of 3-(2,6-dimethylphenoxy)-4-methoxypyridazine 1-oxide obtained in (2),1.10 mL (8.25 mmol) of trimethylsilylcyanide and 2.00 mL (14.4 mmol) oftriethylamine were added to the solution, and the resulting mixture wasstirred at 90° C. for 1 hour and 30 minutes. The reaction mixture waspoured into a saturated aqueous ammonium chloride solution, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the residue was purified by silicagel column chromatography to obtain 0.675 g (2.65 mmol, Yield: 90.8%) of6-(2,6-dimethylphenoxy)-5-methoxy-3-pyridazinecarbonitrile.

(4) 6-(2,6-Dimethylphenoxy)-5-hydroxy-3-pyridazinecarbonitrile (CompoundNo. 2453, Step M-2)

In acetonitrile (5 mL) was dissolved 0.500 g (1.96 mmol) of6-(2,6-dimethylphenoxy)-5-methoxy-3-pyridazinecarbonitrile obtained in(3), 0.300 mL (2.36 mmol) of trimethylsilyl chloride and 0.350 g (2.33mmol) of sodium iodide were added to the solution, and the resultingmixture was stirred at room temperature. 5 mL of acetonitrile wasadditionally added and the resulting mixture was stirred for 1 hour,then, 3 mL of 1,4-dioxane was added thereto, and the resulting mixturewas stirred overnight. The reaction mixture was poured into an aqueoussodium sulfite solution, and made acidic by adding 1 mol/L hydrochloricacid. The resulting mixture was extracted with dichloromethane, washedwith brine, and dried over anhydrous sodium sulfate. The solvent wasremoved, and the residue was purified by silica gel columnchromatography to obtain 0.121 g (0.502 mmol, Yield: 25.6%) of6-(2,6-dimethylphenoxy)-5-hydroxy-3-pyridazinecarbonitrile (Compound No.2453).

¹H-NMR (90 MHz, CDCl₃) δ ppm: 11.3 (1H, brs), 7.09-6.99 (4H, m), 1.90(6H, s). Appearance: amorphous.

EXAMPLE 39 1-[5-Hydroxy-6-(2-methylphenoxy)-3-pyridazinyl]-ethanone(Compound No. 2455) (1)6-(1-Ethoxyvinyl)-4-methoxy-3-(2-methylphenoxy)-pyridazine (Step L-1)

In toluene (6.5 mL) was dissolved 321 mg (1.28 mmol) of6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2(1), 534 mg (1.48 mmol) of (1-ethoxyvinyl)(tributyl)tin, then 155.3 mg(0.134 mmol) of tetrakis(triphenylphosphine)palladium were successivelyadded to the solution at room temperature, and the resulting mixture wasrefluxed for 3 hours and 20 minutes. The reaction mixture was allowed tostand at room temperature overnight, then, ethyl acetate, water andsodium fluoride were added to the mixture and the resulting mixture wasstirred for 2 hours. The mixture was filtered through Celite, ethylacetate was added to the filtrate, and the organic layer was separated,and washed successively with water and brine. After drying overanhydrous sodium sulfate, the solvent was removed. The obtained residuewas purified by silica gel column chromatography (hexane:ethyl acetate,gradient) to obtain 51.8 mg (0.181 mmol, Yield: 14.1%) of6-(1-ethoxyvinyl)-4-methoxy-3-(2-methylphenoxy)pyridazine.

(2) 1-[5-Hydroxy-6-(2-methylphenoxy)-3-pyridazinyl]ethanone (CompoundNo. 2455, Step L-2)

In dimethylsulfoxide (2 mL) was dissolved 18.4 mg (0.194 mmol) of2-hydroxypyridine, 21.7 mg (0.194 mmol) of potassium tert-butoxide wasadded to the solution at room temperature, and the resulting mixture wasstirred at room temperature for 10 minutes. To the mixture was added adimethylsulfoxide (3 mL) solution containing 50.4 mg (0.176 mmol) of6-(1-ethoxyvinyl)-4-methoxy-3-(2-methylphenoxy)-pyridazine obtained in(1), and the resulting mixture was stirred at 100° C. for 8 hours and at130° C. for 5 hours and 30 minutes. Moreover, 18.4 mg (0.194 mmol) of2-hydroxypyridine, then 21.7 mg (0.194 mmol) of potassium tert-butoxidewere additionally added to the mixture, and the resulting mixture wasstirred at 130° C. for 2 hours. The reaction mixture was allowed tostand for cooling, and after adding water, and the mixture was washedwith ethyl acetate. The aqueous layer was made acidic with 4 mol/Lhydrochloric acid, and extracted with ethyl acetate. The organic layerswere combined, dried over anhydrous sodium sulfate, and the solvent wasremoved. The obtained residue was purified by preparative thin-layerchromatography (available from Merck Co., 1.05744, 3 plates were used,developed by ethyl acetate) to obtain 28.5 mg (0.117 mmol, Yield: 66.5%)of 1-[5-hydroxy-6-(2-methylphenoxy)-3-pyridazinyl]ethanone (Compound No.2455).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.48-7.05 (5H, m), 2.58 (3H, s), 2.10(3H, s). Melting point (° C.): 182-185.

EXAMPLE 40 3-(2-Methylphenoxy)-6-phenyl-4-pyridazinol (Compound No.2464) (1) 4-Methoxy-3-(2-methylphenoxy)-6-phenylpyridazine (Step L-1)

210 mg (0.837 mmol) of 6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazineobtained in Example 2 (1), toluene (4 mL) and water (0.5 mL) were mixed,161 mg (1.32 mmol) of phenylboronic acid, 365 mg (2.64 mmol) ofpotassium carbonate and 102 mg (0.0879 mmol) oftetrakis(triphenylphosphine)palladium were successively added to themixture at room temperature, and the resulting mixture was refluxed for2 hours and 50 minutes. The reaction mixture was allowed to stand atroom temperature overnight, the mixture was filtered through Celite, andethyl acetate and water were added to the filtrate. The organic layerwas separated, washed with brine. After drying over anhydrous sodiumsulfate, the solvent was removed. The obtained residue was purified bysilica gel column chromatography (eluted with hexane:ethyl acetate=3:1)to obtain 146 mg (0.500 mmol, Yield: 59.7%) of4-methoxy-3-(2-methylphenoxy)-6-phenylpyridazine.

(2) 3-(2-Methylphenoxy)-6-phenyl-4-pyridazinol (Compound No. 2464, StepL-2)

In dimethylsulfoxide (1.5 mL) was dissolved 91.9 mg (0.966 mmol) of2-hydroxypyridine, 95.4 mg (0.850 mmol) of potassium tert-butoxide wasadded to the solution at room temperature, and the resulting mixture wasstirred at room temperature for 10 minutes. To the mixture was added adimethylsulfoxide (1 mL) solution containing 82.8 mg (0.283 mmol) of4-methoxy-3-(2-methylphenoxy)-6-phenylpyridazine obtained in (1), andthe resulting mixture was stirred at 60° C. for 3 hours. The reactionmixture was allowed to stand for cooling, and after adding water, themixture was washed with ethyl acetate. The aqueous layer was made acidicwith 4 mol/L hydrochloric acid, and extracted with ethyl acetate. Theorganic layers were combined, washed with brine, and dried overanhydrous sodium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom Merck Co., 1.05744, 3 plates were used, developed by ethyl acetate)to obtain 70.8 mg (0.255 mmol, Yield: 90.1%) of3-(2-methylphenoxy)-6-phenyl-4-pyridazinol (Compound No. 2464).

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.78-7.66 (2H, m), 7.58-7.48 (3H, m),7.35-7.08 (4H, m), 6.69 (1H, s), 2.15 (3H s). Melting point (° C.):236-237.

EXAMPLE 41 3,6-Bis(2-fluorophenoxy)-4-pyridazinol (Compound No. 2485)(1) 3,6-Bis(2-fluorophenoxy)pyridazine

In dimethylsulfoxide (20 mL) was dissolved 2.69 g (24.0 mmol) of2-fluorophenol, and 2.69 g (24.0 mmol) of potassium tert-butoxide wasadded to the solution at room temperature. To the mixture was added 1.49g (10.0 mmol) of 2,6-dichloropyridazine, and the resulting mixture wasstirred at 100° C. for 3 hours. The reaction mixture was allowed tostand for cooling, pouted into ice-cold water, and extracted with ethylacetate. The organic layers were combined, washed successively with 1mol/L aqueous sodium hydroxide solution, water and brine, and dried overanhydrous sodium sulfate. The solvent was removed, the obtained residuewas washed with a hot hexane, and then with a hot isopropyl ether toobtain 1.71 g (5.70 mmol, Yield: 57.0%) of3,6-bis(2-fluorophenoxy)pyridazine.

(2) 3,6-Bis(2-fluorophenoxy)pyridazine 1-oxide (Step C-1)

In dry dichloromethane (40 mL) was dissolved 4.14 g (13.8 mmol) of3,6-bis(2-fluorophenoxy)pyridazine obtained in (1), 3.19 g (14.8 mmol)of 80% m-chloroperbenzoic acid was added to the solution, and theresulting mixture was stirred at room temperature for 7 days. Thereaction mixture was poured into ice-cold 1 mol/L aqueous sodiumhydroxide solution, and extracted with ethyl acetate. The organic layerswere combined, washed successively with water and brine, and dried overanhydrous sodium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel column chromatography (eluted withhexane:ethyl acetate=3:1) to obtain 2.24 g (7.09 mmol, Yield: 51.4%) of3,6-bis(2-fluorophenoxy)pyridazine 1-oxide.

(3) 4-Chloro-3,6-bis(2-fluorophenoxy)pyridazine (Step C-2)

2.20 g (6.96 mmol) of 3,6-bis(2-fluorophenoxy)pyridazine 1-oxideobtained in (2) and 50 mL of phosphorus oxychloride were mixed, and themixture was stirred at 90° C. for 1 hour. The reaction mixture wasallowed to stand for cooling, poured into ice-cold water, and extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with 1 mol/L aqueous sodium hydroxide solution, water andbrine, and dried over anhydrous sodium sulfate. The solvent was removed,and the obtained residue was purified by silica gel columnchromatography (hexane:ethyl acetate=10:1) to obtain 1.95 g (5.82 mmol,Yield: 83.6%) of 4-chloro-3,6-bis(2-fluorophenoxy)pyridazine.

(4) 3,6-Bis(2-fluorophenoxy)-4-methoxypyridazine (Step C-3)

In methanol (20 mL) was dissolved 1.44 g (4.30 mmol) of4-chloro-3,6-bis(2-fluorophenoxy)pyridazine obtained in (3), 0.206 g(4.72 mmol) of 55% sodium hydride was added to the solution, and theresulting mixture was stirred at 60° C. for 1 hour. The reaction mixturewas allowed to stand for cooling, poured into ice-cold water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (eluted with hexane:ethylacetate=10:1) to obtain 1.03 g (3.12 mmol, Yield: 72.6%) of3,6-bis(2-fluorophenoxy)-4-methoxypyridazine.

(5) 3,6-Bis(2-fluorophenoxy)-4-pyridazinol (Compound No. 2485, Step C-4)

450 mg (1.36 mmol) of 3,6-bis(2-fluorophenoxy)-4-methoxypyridazineobtained in (4), 77 mg (1.85 mmol) of 96% sodium hydroxide,dimethylsulfoxide (5 mL) and water (1 mL) were mixed, and the mixturewas stirred at 90° C. for 2 hours. The reaction mixture was poured intoice-cold water, and made acidic with hydrochloric acid. The mixture wasextracted with ethyl acetate, washed with water, and dried overanhydrous sodium sulfate. The solvent was removed to obtain 0.380 g(1.20 mmol, Yield: 88.2%) of 3,6-bis(2-fluorophenoxy)-4-pyridazinol(Compound No. 2485).

¹H-NMR. (60 MHz, DMSO-d₆) δ ppm: 7.60-7.08 (8H, m), 6.34 (1H, brs).Melting point (° C.): 228.

EXAMPLE 42(2,4-Dichlorophenyl)(5-{[5-hydroxy-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-1,3-dimethyl-1H-pyrazol-4-yl)methanone(Compound No. 2506) (1)(5-{[5-Chloro-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-1,3-dimethyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)meth

109 mg (0.382 mmol) of(2,4-dichlorophenyl)(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)methanone,1.62 g (6.35 mmol) of 4,6-dichloro-3-(2-methylphenoxy)pyridazineobtained in Example 1 (2) and 107 mg (0.775 mmol) of potassium carbonatewere mixed, and the mixture was stirred at 130° C. for 14 hours. Thereaction mixture was cooled up to room temperature, and purified bysilica gel column chromatography (hexane:ethyl acetate, gradient) toobtain 155 mg (0.308 mmol, Yield: 80.6%) of(5-{[5-chloro-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-1,3-dimethyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone.

(2)(2,4-Dichlorophenyl)(5-{[5-hydroxy-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-1,3-dimethyl-1H-pyrazol-4-yl)met(Compound No. 2506, A-3 Step)

12.3 mg (0.0244 mmol) of(5-{[5-chloro-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-1,3-dimethyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanoneobtained in (1), 0.2 mL of dimethylsulfoxide and 0.012 mL of 10% (W/V)aqueous sodium hydroxide solution were mixed, and the mixture wasstirred at room temperature overnight. The reaction mixture was pouredinto ice-cold water, made acidic by hydrochloric acid, and extractedwith ethyl acetate. The organic layers were combined, and dried overanhydrous sodium sulfate. The solvent was distilled off and the residuewas purified by preparative thin-layer chromatography (available fromMerck Co., 1.05744, developed by dichloromethane:methanol=10:1) toobtain 3.2 mg (0.00784 mmol, Yield: 32%) of(2,4-dichlorophenyl)(5-{[5-hydroxy-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-1,3-dimethyl-1H-pyrazol-4-yl)methanone(Compound No. 2506) and 10.5 mg (0.0208 mmol, Yield: 85.4%) of4-[{[5-chloro-6-(2-methylphenoxy)-3-pyridazinyl]oxy}-(2,4-dichlorophenyl)methylene]-2,5-dimethyl-2,4-dihydro-3H-pyrazol-3-one.

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.36-7.04 (7H, m), 6.20 (1H, brs), 3.64(3H, s), 2.31 (3H, s), 2.20 (3H, s). Appearance: amorphous.

Also, the following compounds were produced in accordance with theabove-mentioned Examples 1 to 42 or by the methods or in accordance withthe methods described in the following Examples 622 to 646.

EXAMPLE 43 3-Phenoxy-4-pyridazinol (Compound No. 1)

¹H-NMR (90 MHz, DMSO-d₆) δ ppm: 12.66 (1H, brs), 8.21 (1H, d, J=6.6 Hz),7.09-7.54 (5H, m), 6.38 (1H, d, J=6.6 Hz). Melting point (° C.): 193.5.

EXAMPLE 446-Chloro-3-{2-[1-(methoxymethyl)cyclopropyl]phenoxy}-4-pyridazinol(Compound No. 163)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.47-7.35 (1H, m), 7.32-7.02 (3H, m),6.71 (1H, s), 3.47 (2H, s), 3.21 (3H, s), 0.80-0.70 (4H, m). Meltingpoint (° C.): 187-190.

EXAMPLE 45 3-(2-Isopropylphenoxy)-4-pyridazinol (Compound No. 6)

¹H-NMR (90 MHz, DMSO-d₆) δ ppm: 12.65 (1H, brs), 8.29 (2H, d, J=6.6 Hz),7.49-6.98 (4H, m), 6.36 (1H, d, J=6.6 Hz), 3.20-2.89 (1H, m, J=6.6 Hz),1.16 (6H, d, J=6.6 Hz). Melting point (° C.): 181.5-182.

EXAMPLE 46 6-Chloro-3-[2-(1-methoxycyclopropyl)phenoxy]-4-pyridazinol(Compound No. 202)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.50-7.10 (4H, m), 6.67 (1H, s), 3.03(3H, s), 1.00-0.85 (4H, m). Melting point (° C.): 157-165.

EXAMPLE 472-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-cyclopropanecarbonitrile(Compound No. 226)

Trans isomer:

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.40-7.10 (4H, m), 6.75 (1H, s),2.65-2.50 (1H, m), 1.65-1.45 (3H, m). Melting point (° C.): 203-207.

Cis isomer:

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.40-7.15 (4H, m), 6.64 (1H, s), 2.59(1H, q, J=8.4 Hz), 2.05-1.90 (1H, m), 1.67-1.40 (2H, m). Melting point(° C.): 225-227.

EXAMPLE 48 6-Chloro-3-phenoxy-4-pyridazinol (Compound No. 123)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.60-7.00 (5H, m), 6.87 (1H, s). Meltingpoint (° C.): 222-224.

EXAMPLE 49 6-Chloro-3-(2-fluorophenoxy)-4-pyridazinol (Compound No. 124)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.50-7.05 (4H, m), 6.70 (1H, s). Meltingpoint (° C.): 210-212.

EXAMPLE 50 6-Chloro-3-(2-chlorophenoxy)-4-pyridazinol (Compound No. 125)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.70-7.10 (4H, m), 6.95 (1H, s). Meltingpoint (° C.): 208-212.

EXAMPLE 51 3-(2-Bromophenoxy)-6-chloro-4-pyridazinol (Compound No. 126)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.68 (1H, dd, J=7.5, 1.8 Hz), 7.53-7.10(3H, m), 6.73 (1H, s). Melting point (° C.): 201-203.

EXAMPLE 52 6-Chloro-3-(2-iodophenoxy)-4-pyridazinol (Compound No. 127)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.89 (1H, dd, J=7.7, 1.5 Hz) 7.45 (1H,td, J=7.7, 1.5 Hz), 7.22 (1H, dd, J=7.7, 1.5 Hz), 7.04 (1H, td, J=7.7,1.5 Hz), 6.74 (1H, s). Melting point (° C.): 216-217.

EXAMPLE 53 6-Chloro-3-[2-(2-ethoxycyclopropyl)phenoxy]-4-pyridazinol(Compound No. 249)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.26-7.05 (4H, m), 6.68 (1H, s), 3.46(1H, q, J=5.2 Hz), 3.30-3.15 (2H, m), 2.17-1.96 (1H, m), 1.10 (2H, dd,J=5.2 Hz, 8.5 Hz), 0.93 (3H, t, J=7.0 Hz). Melting point (° C.):145-152.

EXAMPLE 54 6-Chloro-3-[2-(2,2-difluorocyclopropyl)phenoxy]-4-pyridazinol(Compound No. 264)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.40-7.15 (4H, m), 6.72 (1H, s),2.85-2.65 (1H, m), 1.90-1.65 (2H, s). Melting point (° C.): 215-216.

EXAMPLE 55 6-Chloro-3-(2-ethylphenoxy)-4-pyridazinol (Compound No. 130)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.35-7.15 (3H, m), 7.10-7.02 (1H, m),6.70 (1H, s), 2.56 (2H, q, J=7.7 Hz), 1.17 (3H, t, J=7.7 Hz). Meltingpoint (° C.): 217-218.

EXAMPLE 56 6-Chloro-3-(2-propylphenoxy)-4-pyridazinol (Compound No. 131)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.45-7.05 (4H, m), 6.90 (1H, s),3.00-2.35 (2H, m), 1.95-1.26 (2H, m), 1.05-0.68 (3H, m). Melting point(° C.): 170-172.

EXAMPLE 57 6-Chloro-3-(2-isopropylphenoxy)-4-pyridazinol (Compound No.132)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.60-7.00 (4H, m), 6.92 (1H, s), 3.11(1H, septet, J=7.0 Hz), 1.18 (6H, d, J=7.0 Hz). Melting point (° C.):183.

EXAMPLE 58 3-(2-Butylphenoxy)-6-chloro-4-pyridazinol (Compound No. 133)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 11.8 (1H, brs), 7.30-6.70 (4H, m), 6.53(1H, s), 2.60-2.00 (2H, m), 1.80-0.60 (7H, m). Melting point (° C.):149.5-150.

EXAMPLE 59 6-Chloro-3-(2-isobutylphenoxy)-4-pyridazinol (Compound No.134)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 12.90 (1H, brs), 7.40-6.85 (4H, m), 6.50(1H, s), 2.25 (2H, d, J=10.0 Hz), 2.20-1.45 (1H, m, J=10.0 Hz), 0.75(6H, d, J=10.0 Hz). Melting point (° C.): 151.5-152.5.

EXAMPLE 60 3-(2-s-Butylphenoxy)-6-chloro-4-pyridazinol (Compound No.135)

¹H-NMR (60 MHz, CDCl₃+DMF-d₇) δ ppm: 7.35-6.80 (4H, m), 6.60 (1H, s),3.05-2.50 (1H, m), 1.80-1.25 (2H, m), 1.13 (3H, d, J=6.2 Hz), 0.95-0.50(3H, m). Melting point (° C.): 158-159.

EXAMPLE 61 3-(2-tert-Butylphenoxy)-6-chloro-4-pyridazinol (Compound No.136)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.55-6.85 (4H, m), 6.91 (1H, s), 5.32(1H, brs), 1.35 (9H, s). Melting point (° C.): 215-216.

EXAMPLE 62 6-Chloro-3-(2-pentylphenoxy)-4-pyridazinol (Compound No. 137)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 11.70 (1H, brs), 7.40-6.80 (4H, m), 6.50(1H, s), 2.60-2.20 (2H, m), 1.80-0.60 (9H, m). Melting point (° C.):151.5-152.5.

EXAMPLE 63 6-Chloro-3-(2-hexylphenoxy)-4-pyridazinol (Compound No. 138)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.40-6.70 (4H, m), 6.53 (1H, s), 2.70-2.20(2H, m), 2.00-0.60 (11H, m). Melting point (° C.): 118-118.5.

EXAMPLE 64 6-Chloro-3-[2-(2,2-dichlorocyclopropyl)phenoxy]-4-pyridazinol(Compound No. 265)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.55-7.15 (4H, m), 6.69 (1H, s), 2.90(1H, dd, J=11.0, 10.8 Hz), 2.05-1.85 (2H, m). Melting point (° C.):158-163.

EXAMPLE 65 6-Chloro-3-[2-(2,2-dibromocyclopropyl)phenoxy]-4-pyridazinol(Compound No. 266)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.41-7.36 (1H, m), 7.29-7.13 (3H, m),6.71 (1H, s), 2.97-2.87 (1H, dd, J=11.0, 8.4 Hz), 2.21-2.01 (2H, m).Melting point (° C.): 208-210 (decomposed).

EXAMPLE 66 6-Chloro-3-[2-(1-methylcyclopropyl)phenoxy]-4-pyridazinol(Compound No. 144)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.40-7.35 (1H, m), 7.22-7.17 (2H, m),6.99-6.94 (1H, m), 6.59 (1H, s), 1.25 (3H, s), 0.85-0.60 (2H, m),0.60-0.45 (2H, m). Melting point (° C.): 196-198.

EXAMPLE 67 6-Chloro-3-[2-(1-ethylcyclopropyl)phenoxy]-4-pyridazinol(Compound No. 145)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.35-7.10 (3H, m), 6.98 (1H, br.d, J=7.3Hz), 6.59 (1H, s), 1.50 (2H, q, J=7.0 Hz), 1.26 (3H, t, J=7.0 Hz),0.67-0.50 (4H, m). Melting point (° C.): 162-165.

EXAMPLE 686-Chloro-3-{2-[1-(cyclopropyl)cyclopropyl]phenoxy}-4-pyridazinol(Compound No. 151)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.35-7.29 (1H, m), 7.26-7.10 (2H m),7.00-6.92 (1H, m), 6.58 (1H, s), 1.30-1.15 (1H, m), 0.60-0.40 (4H, m),0.27-0.15 (2H, m), 0.07-0.00 (2H, m). Melting point (° C.): 180-182.

EXAMPLE 691-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-cyclopropanecarbonitrile(Compound No. 173)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.55-7.15 (5H, m), 1.65-1.20 (4H, m).Melting point (° C.): 63-64.

EXAMPLE 70 6-Chloro-3-[2-(1-phenylcyclopropyl)phenoxy]-4-pyridazinol(Compound No. 184)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.65-7.55 (1H, m), 7.28-7.20 (2H, m),7.17-6.95 (6H, m), 6.41 (1H, s), 1.19 (4H, s). Melting point (° C.):172-173.

EXAMPLE 71 6-Chloro-3-(2-isopropenylphenoxy)-4-pyridazinol (Compound No.304)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.36-7.10 (4H, m), 6.66 (1H, s), 5.06(1H, br.s), 5.02 (1H, br.s), 2.01 (3H, d, J=1.5 Hz). Melting point (°C.): 187-188.

EXAMPLE 72 6-Chloro-3-[2-(2-methylcyclopropyl)phenoxy]-4-pyridazinol(Compound No. 217)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.32-6.97 (4H, m), 6.82 (1H, brs),1.89-1.78 (0.8H, m), 1.52-1.43 (0.2H, m), 1.05-0.60 (6H, m). Meltingpoint (° C.): 192-208.

EXAMPLE 73 6-Chloro-3-[2-(2-ethoxycyclopropyl)phenoxy]-4-pyridazinol(Compound No. 249)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.30-7.05 (4H, m), 6.68 (1H, s),3.51-3.15 (3H, m), 2.07-1.95 (1H, m), 1.13-1.06 (2H, m), 0.93 (3H, t,J=7.1 Hz). Melting point (° C.): 145-152.

EXAMPLE 74(2E)-3-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-phenyl}acrylonitrile(Compound No. 306)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.80-7.40 (3H, m), 7.35-7.15 (2H, m),6.72 (1H, s), 6.30 (1H, d, J=6.9 Hz). Melting point (° C.): 190-192.

EXAMPLE 75 6-Chloro-3-[2-(2,2-dimethylcyclopropyl)phenoxy]-4-pyridazinol(Compound No. 267)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.30-7.10 (4H, m), 1.57 (1H, dd, J=8.4,6.2 Hz), 0.91-0.85 (1H, m), 0.85 (3H, s), 0.72-0.65 (1H, m), 0.65 (3H,s). Melting point (° C.): 187-188.

EXAMPLE 76 6-Chloro-3-{2-[(cis-2,cis-3-dimethyl)-ref-1-cyclopropyl]phenoxy}-4-pyridazinol (Compound No.269)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.36-7.11 (4H, m), 6.68 (1H, s), 1.60(1H, t, J=8.4 Hz), 1.09-0.93 (8H, m). Appearance: amorphous.

EXAMPLE 77 6-Chloro-3-{2-[(cis-2,trans-3-dimethyl)-ref-1-cyclopropyl]phenoxy}-4-pyridazinol (Compound No.270)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.30-7.09 (4H, m), 6.80 (1H, brs),1.56-1.50 (1H, m), 1.10-0.95 (1H, m), 1.03 (3H, s), 0.80-0.67 (1H, m),0.71 (3H, s). Melting point (° C.): 157-160.

EXAMPLE 78 6-Chloro-3-{2-[(trans-2,trans-3-dimethyl)-ref-1-cyclopropyl]phenoxy}-4-pyridazinol (Compound No.271)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.22-6.96 (4H, m), 6.70 (1H, s),1.18-0.95 (9H, m) Melting point (° C.): 181-183.

EXAMPLE 793-{2-[(ref-1,cis-5,cis-6)-Bicyclo[3.1.0]hex-6-yl]phenoxy}-6-chloro-4-pyridazinol(Compound No. 272)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.40-7.05 (4H, m), 6.68 (1H, s),2.05-1.60 (5H, m), 1.53 (2H, s), 1.35-1.20 (1H, m), 0.25-0.05 (1H, m).Melting point (° C.): 215-240.

EXAMPLE 803-{2-[(ref-1,cis-5,trans-6)-Bicyclo[3.1.0]hex-6-yl]phenoxy}-6-chloro-4-pyridazinol(Compound No. 273)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.20-7.10 (2H, m), 7.10-6.90 (2H, m),6.58 (1H, s), 1.80-1.40 (8H, m), 1.20-1.00 (1H, m). Melting point (°C.): 137-139.

EXAMPLE 813-{2-[(ref-1,cis-6,cis-7)-Bicyclo[4.1.0]hept-7-yl]phenoxy}-6-chloro-4-pyridazinol(Compound No. 274)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.44 (1H, br.d, J=6.3 Hz), 7.35-7.10 (3H,m), 6.66 (1H, s), 2.00-1.50 (5H, m), 1.20-1.00 (4H, m), 0.90-0.65 (2H,m). Melting point (° C.): >260.

EXAMPLE 823-{2-[(ref-1,cis-6,trans-7)-Bicyclo[4.1.0]hept-7-yl]phenoxy}-6-chloro-4-pyridazinol(Compound No. 275)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.20-7.10 (2H, m), 7.05-6.85 (2H, m),6.58 (1H, s), 1.90-1.70 (2H, m), 1.60-1.40 (3H, m), 1.30-1.05 (6H, m).Melting point (° C.): 191-193.

EXAMPLE 83 6-Chloro-3-{2-[(2,2,cis-3-trimethyl)-ref-1-cyclopropyl]phenoxy}-4-pyridazinol (Compound No.279)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.30-7.00 (4H, m), 6.56 (1H, s),1.42-1.22 (2H, m), 1.05-0.70 (9H, m). Melting point (° C.): 118-120.

EXAMPLE 84 6-Chloro-3-{2-[(2,2,trans-3-trimethyl)-ref-1-cyclopropyl]phenoxy}-4-pyridazinol (CompoundNo. 280)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.26-7.06 (4H, m), 6.59 (1H, s),1.70-1.50 (1H, m), 1.30-1.25 (1H, m), 1.09 (3H, s), 0.96 (3H, s), 0.75(3H, s). Melting point (C): 160-162.

EXAMPLE 85 6-Chloro-3-(2-cyclobutylphenoxy)-4-pyridazinol (Compound No.284)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.43-7.30 (1H, m), 7.30-7.18 (2H, m),7.08-6.98 (1H, m), 6.69 (1H, s), 3.68-3.50 (1H, m), 2.25-1.70 (6H, m).Melting point (° C.): 188-189.

EXAMPLE 861-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-cyclobutanecarbonitrile(Compound No. 287)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.50-7.20 (5H, m), 2.70-1.80 (6H, m)Melting point (° C.): 213-215.

EXAMPLE 871-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-cyclobutanecarboxylicacid(Compound No. 288)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.42-7.35 (1H, m), 7.35-7.20 (2H, m),7.08-7.03 (1H, m), 6.66 (1H, s), 2.80-2.45 (4H, m), 2.22-1.95 (1H, m),1.90-1.70 (1H, m). Melting point (° C.): 173-175.

EXAMPLE 88 6-Chloro-3-(2-cyclopentylphenoxy)-4-pyridazinol (Compound No.292)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.41-7.35 (1H, m), 7.25-7.17 (2H, m),7.08-7.02 (1H, m), 6.70 (1H, s), 3.14-3.06 (1H, m), 1.98-1.52 (8H, m).Melting point (° C.): 178-180.

EXAMPLE 89 6-Chloro-3-(2-cyclohexylphenoxy)-4-pyridazinol (Compound No.293)

¹H-NMR (60 MHz, CDCl₃+DMF-d₇) δ ppm: 7.40-6.70 (4H, m), 6.55 (1H s),2.75 (1H, brs), 2.10-0.90 (10H, m). Melting point (° C.): 158-159.

EXAMPLE 90 6-Chloro-3-[2-(trifluoromethyl)phenoxy]-4-pyridazinol(Compound No. 300)

¹H-NMR (90 MHz, CD30D) δ ppm: 7.76-7.27 (4H, m), 6.75 (1H, s), 5.47 (1H,s). Melting point (° C.): 188.

EXAMPLE 91 6-Chloro-3-[2-(1-propenyl)phenoxy}-4-pyridazinol (CompoundNo. 305)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.70-6.90 (5H, m), 6.76 (1H, s),6.50-6.20 (2H, m), 1.81 (3H, d, J=5.0 Hz). Melting point (° C.):204-206.

EXAMPLE 92 3-(2-Allylphenoxy)-6-chloro-4-pyridazinol. (Compound No. 307)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.46-7.24 (4H, m), 6.96 (1H s), 6.20-5.60(1H, m), 5.20-4.80 (2H, m), 3.46-3.26 (2H, m). Melting point (° C.):200-202.5.

EXAMPLE 93 6-Chloro-3-[2-(1-propynyl)phenoxy]-4-pyridazinol (CompoundNo. 309)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.43-7.32 (2H, m), 7.23-7.16 (2H, m),6.73 (1H, s), 1.87 (3H, s). Melting point (° C.): 182-184.

EXAMPLE 94 6-Chloro-3-[2-(cyclopropylmethyl)phenoxy]-4-pyridazinol(Compound No. 311)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.45 (1H, dd, J=7.3, 1.8 Hz), 7.31-7.17(2H, m), 7.10 (1H, dd, J=7.3, 1.8 Hz), 2.38 (2H, d, J=7.0 Hz), 1.00-0.88(1H, m), 0.50-0.40 (2H, m), 0.22-0.11 (2H, m) Melting point (° C.):165-168.

EXAMPLE 95 3-(2-Benzylphenoxy)-6-chloro-4-pyridazinol (Compound No. 315)Melting point (° C.): 185-187. EXAMPLE 966-Chloro-3-[2-(methoxymethyl)phenoxy]-4-pyridazinol (Compound No. 324)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.47 (1H, br.d, J=7.7 Hz), 7.42-7.20(2H, m), 7.15 (1H, br.d, J=7.7 Hz), 6.83 (1H, brs), 4.35 (2H, s), 3.23(3H, s) Melting point (° C.): 211-212.

EXAMPLE 97 6-Chloro-3-[2-(ethoxymethyl)phenoxy]-4-pyridazinol (CompoundNo. 325)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.47 (1H, br.d, J=7.7 Hz), 7.42-7.20(2H, m), 7.16 (1H, br.d, J=7.7 Hz), 6.82 (1H, brs), 4.38 (2H, s), 3.39(2H, q, J=7.0 Hz), 1.03 (3H, t, J=7.0 Hz). Melting point (° C.):173-174.

EXAMPLE 98 6-Chloro-3-[2-(1,3-dioxolan-2-yl)phenoxy]-4-pyridazinol(Compound No. 329) Melting point (° C.): 143-145. EXAMPLE 991-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-ethanoneO-methyloxime (Compound No. 334)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.47 (2H, t, J=7.7 Hz), 7.31 (1H, d,J=7.7 Hz), 7.24 (1H, d, J=7.7 Hz), 6.85 (1H, brs), 3.76 (2.8H, s), 3.58(0.2H, s), 2.02 (2.8H, s), 1.99 (0.2H, Melting point (° C.): 165-167.

EXAMPLE 100 Methyl 2-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]-benzoate(Compound No. 339)

¹H-NMR (60 MHz, CDCl₃+DMF-d₇) δ ppm: 8.10-7.18 (4H, m), 6.80 (1H, s),5.75 (1H, brs), 3.70 (3H, s). Melting point (° C.): 188-191.

EXAMPLE 101 3-([1,1′-Biphenyl]-2-yloxy)-6-chloro-4-pyridazinol (CompoundNo. 344)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.30-6.70 (10H, m), 6.25 (1H, s). Meltingpoint (° C.): 98-100.

EXAMPLE 1026-Chloro-3-{[3′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]oxy}-4-pyridazinol(Compound No. 348)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.65-7.58 (2H, m), 7.51-7.26 (5H, m),7.12-7.06 (1H, m), 6.41 (1H, brs). Appearance: paste state.

EXAMPLE 1036-Chloro-3-{[3′-(trifluoromethyl)[1,1′-biphenyl]-2-yl]oxy}-4-pyridazinol(Compound No. 349)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.71-7.64 (2H, m), 7.55-7.30 (5H, m),7.20-7.13 (1H, m), 6.43 (1H, s). Appearance: paste state.

EXAMPLE 104 6-Chloro-3-[2-(1-pyrrolidinyl)phenoxy]-4-pyridazinol(Compound No. 355)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.19-6.73 (4H, m), 5.64 (1H, s),3.32-3.25 (4H, m), 1.91-1.84 (4H, m). Appearance: amorphous.

EXAMPLE 105 6-Chloro-3-[2-(1H-pyrrol-1-yl)phenoxy]-4-pyridazinol(Compound No. 356)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.41-7.27 (4H, m), 6.95-6.93 (2H, m),6.46 (1H, m), 6.10-6.08 (2H, m). Appearance: amorphous.

EXAMPLE 106 6-Chloro-3-[2-(2-thienyl)phenoxy]-4-pyridazinol (CompoundNo. 359)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.68-7.60 (1H, m), 7.45-7.05 (5H, m),7.01-6.95 (1H, m), 6.52 (1H, s). Appearance: amorphous.

EXAMPLE 107 6-Chloro-3-[2-(3-thienyl)phenoxy]-4-pyridazinol (CompoundNo. 361)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.46-7.37 (3H, m), 7.30-7.15 (4H, m).Melting point (° C.): 207-209.

EXAMPLE 108 6-Chloro-3-[2-(1H-pyrazol-1-yl)phenoxy]-4-pyridazinol(Compound No. 362)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.09 (1H, d, J=2.2 Hz), 7.70 (1H, dd,J=7.5, 2.4 Hz), 7.62 (1H, d, J=2.2 Hz), 7.50-7.27 (3H, m), 6.55 (1H, s),6.39 (1H, t, J=2.2 Hz). Appareance: amorphous.

EXAMPLE 1086-Chloro-3-[2-(3,5-dimethyl-1H-pyrazol-1-yl)phenoxy]-4-pyridazinol(Compound No. 364)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.60-7.32 (4H, m), 6.52 (1H, s), 5.86(1H, s), 2.17 (3H, s), 2.10 (3H, s). Appareance: amorphous.

EXAMPLE 1096-Chloro-3-{2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy}-4-pyridazinol(Compound No. 365)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.79 (1H, brs), 7.70-7.35 (5H, m), 7.06(1H, brs), 6.68 (1H, s). Appareance: amorphous.

EXAMPLE 1116-Chloro-3-{2-[4-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy}-4-pyridazinol(Compound No. 366)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 8.75 (1H, s), 8.11 (1H, s), 7.80-7.74(1H, m), 7.58-7.38 (3H, m), 6.77 (1H, s). Appareance: oily product.

EXAMPLE 1126-Chloro-3-{2-[5-(trifluoromethyl)-1H-pyrazol-1-yl]phenoxy}-4-pyridazinol(Compound No. 367)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 8.30 (1H, brs), 7.83-7.72 (1H, m),7.60-7.40 (3H, m), 6.91 (1H, br.d, J=2.6 Hz), 6.78 (1H, s). Appearance:amorphous.

EXAMPLE 1135-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-N,N-dimethyl-1H-pyrazole-1-sulfonamide(CompoundNo. 369)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.87 (1H, d, J=2.6 Hz), 7.78 (1H, dd,J=7.3, 1.8 Hz), 7.65-7.35 (3H, m), 7.20 (1H, s), 7.03 (1H, d, J=2.6 Hz),2.86 (6H, s). Melting point (° C.): 151-152.

EXAMPLE 1143-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-N,N-dimethyl-1H-pyrazole-1-sulfonamide(CompoundNo. 368)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.19 (1H, d, J=2.9 Hz), 8.12 (1H, s),7.97 (1H, dd, J=7.3, 2.2 Hz), 7.61 (1H, d, J=1.5 Hz), 7.50-7.33 (2H, m),6.98 (1H, d, J=2.9 Hz), 2.83 (6H, s). Melting point (° C.): 210-212.

EXAMPLE 1156-Chloro-3-[2-(4-methyl-1,3-thiazol-2-yl)phenoxy]-4-pyridazinol(Compound No. 370)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.17 (1H, d, J=7.7 Hz), 7.73 (1H, d,J=7.7 Hz), 7.47 (1H, t, J=7.7 Hz), 7.28 (1H, t, J=7.7 Hz), 7.02 (1H, s),6.98 (1H, s), 2.56 (3H, s). Appearance: amorphous.

EXAMPLE 116 3-[2-(1,3-Benzoxazol-2-yl)phenoxy]-6-chloro-4-pyridazinol(Compound No. 375)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.31 (1H, dd, J=7.9, 1.6 Hz), 7.73-7.30(7H, m), 6.78 (1H, s). Melting point (° C.): 165-167.

EXAMPLE 117 353-[2-(1,3-Benzothiazol-2-yl)phenoxy]-6-chloro-4-pyridazinol (CompoundNo. 376)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.12 (1H, d, J=7.7 Hz), 8.00-7.84 (1H,m), 7.78 (1H, d, J=7.7 Hz), 7.62-7.05 (1H, brs). Melting point (° C.):215-217.

EXAMPLE 118 6-Chloro-3-[2-(dimethylamino)phenoxy]-4-pyridazinol(Compound No. 379)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.17-6.96 (4H, m), 6.61 (1H, s), 2.75(6H, s). Appareance: amorphous.

EXAMPLE 119 6-Chloro-3-(2-nitrophenoxy)-4-pyridazinol (Compound No. 383)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.16 (1H, d, J=6.0 Hz), 7.90-7.33 (3H,m), 6.78 (1H, s). Melting point (° C.): 99-100.

EXAMPLE 120 6-Chloro-3-(2-ethynylphenoxy)-4-pyridazinol (Compound No.308)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.57-7.41 (2H, m), 7.30-7.20 (2H, m),6.71 (1H, s), 3.60 (1H, s). Melting point (° C.): 189-191.

EXAMPLE 121 6-Chloro-3-(2-methoxyphenoxy)-4-pyridazinol (Compound No.385)

¹H-NMR (60 MHz, CDCl₃+DMF-d₇) δ ppm: 7.30-6.80 (4H, m), 6.55 (1H, s),3.69 (3H, s) Melting point (° C.): 191-194.

EXAMPLE 122 6-Chloro-3-(2-ethoxyphenoxy)-4-pyridazinol (Compound No.386)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.26-7.02 (2H, m), 6.98-6.85 (2H, m),6.57 (1H, s), 5.35 (1H, brs), 3.92 (2H, q, J=7.0 Hz), 1.18 (t, 3H, J=7.0Hz). Melting point (° C.): 155-175.

EXAMPLE 123 6-Chloro-3-(2-isopropoxyphenoxy)-4-pyridazinol (Compound No.387)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.28-7.10 (3H, m), 6.97 (1H, td, J=7.3,2.3 Hz), 6.83 (1H, brs), 4.52 (1H, septet, J=6.2 Hz), 1.07 (6H, d, J=6.2Hz). Melting point (° C.): 178-1.79.

EXAMPLE 124 6-Chloro-3-[2-(difluoromethoxy)phenoxy]-4-pyridazinol(Compound No. 390)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.40 (4H, s), 6.63 (1H, s) 6.53 (1H, t,J=73.8 Hz). Melting point (° C.): 210-212.

EXAMPLE 125 6-Chloro-3-[2-(trifluoromethoxy)phenoxy]-4-pyridazinol(Compound No. 391)

¹H-NMR (200 MHz, CDCl₃+CD₃OD) δ ppm: 7.38-7.20 (4H, m), 6.60 (1H, s).Melting point (° C.): 215.

EXAMPLE 126 6-Chloro-3-[2-(2-methoxyethoxy)phenoxy]-4-pyridazinol(Compound No. 396)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.26-6.93 (4H, m), 6.62 (1H, s),4.78-4.03 (2H, m), 3.55-3.50 (2H, m), 3.24 (3H, s). Appareance: pastestate.

EXAMPLE 127 6-Chloro-3-[2-(2-hydroxyphenoxy)phenoxy]-4-pyridazinol(Compound No. 399)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.27-6.75 (8H, m), 6.61 (1H, s).Appareance: amorphous.

EXAMPLE 1286-Chloro-3-{2-{2-[(6-chloro-4-ethoxy-3-pyridazinyl)-oxy]phenoxy}phenoxy}-4-pyridazinol(Compound No. 400)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.65-6.70 (8H, m), 6.63-6.59 (2H, m),4.19 (2H, q, J=7.0 Hz), 1.50 (3H, t, J=7.0 Hz). Appareance: amorphous.

EXAMPLE 129 6-Chloro-3-[2-(methylsulfanyl)phenoxy]-4-pyridazinol(Compound No. 401)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.43-7.11 (4H, m), 6.71 (1H, s), 2.40(3H, s). Melting point (° C.): 174-175.

EXAMPLE 130 6-Chloro-3-[2-(isopropylsulfanyl)phenoxy]-4-pyridazinol(Compound No. 403) Melting point (° C.): 176-177. EXAMPLE 1316-Chloro-3-(2-cyanophenoxy)-4-pyridazinol (Compound No. 330)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.82-7.68 (2H, m), 7.46-7.34 (2H, m),6.79 (1H, s) Appareance: amorphous.

EXAMPLE 1321-{2-[6-Chloro-4-hydroxy-3-pyridazinyl]oxy}phenyl}-ethanone(Compound No.336)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.88-7.85 (1H, m), 7.65-7.57 (1H, m),7.43-7.26 (2H, m), 6.73 (1H, s), 2.50 (3H, br.s). Melting point (° C.):186-189.

EXAMPLE 133 6-Chloro-3-(3-chlorophenoxy)-4-pyridazinol (Compound No.410)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.45-7.10 (5H, m), 6.72 (1H, s). Meltingpoint (° C.): 217.

EXAMPLE 134 6-Chloro-3-(3-iodophenoxy)-4-pyridazinol (Compound No. 412)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.64-7.53 (2H, m), 7.28-6.70 (3H, m).Melting point (° C.): 202-203.

EXAMPLE 135 6-Chloro-3-(3-methylphenoxy)-4-pyridazinol (Compound No.413)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.35-6.80 (4H, m), 6.95 (1H, s), 2.35(3H, s). Melting point (° C.): 205-208.

EXAMPLE 136 6-Chloro-3-(3-isopropylphenoxy)-4-pyridazinol (Compound No.415) Melting point (° C.): 176-177. EXAMPLE 1373-(3-tert-Butylphenoxy)-6-chloro-4-pyridazinol (Compound No. 416)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 7.40-6.65 (4H, m), 6.67 (1H, s), 1.27(9H, s). Melting point (° C.): 203-207.

EXAMPLE 138 6-Chloro-3-(3-cyclopropylphenoxy)-4-pyridazinol (CompoundNo. 417)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.35-7.20 (1H, m), 6.98-6.85 (3H, m),6.78 (1H, brs), 2.00-1.88 (1H, m), 0.98-0.87 (2H, m), 0.70-0.60 (2H, m).Melting point (° C.): 179-181.

EXAMPLE 139 6-Chloro-3-[3-(trifluoromethyl)phenoxy]-4-pyridazinol(Compound No. 418)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.70-7.40 (4H, m), 6.95 (1H, s). Meltingpoint (° C.): 213-216.

EXAMPLE 140 6-Chloro-3-[3-(2-furyl)phenoxy]-4-pyridazinol (Compound No.419)

¹H-NMR (200 MHz, CDCl₃+CD₃OD) δ ppm: 7.55-7.35 (4H, m), 7.08-7.02 (1H,m), 6.67 (1H, d, J=3.3 Hz), 6.59 (1H, brs), 6.48 (1H, dd, J=3.3, 1.8Hz). Melting point (° C.): 200-202.

EXAMPLE 141 3-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]benzonitrile(Compound No. 420)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.70-7.40 (4H, m), 6.75 (1H, s). Meltingpoint (° C.): 226-229.

EXAMPLE 142 3-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]benzaldehyde(Compound No. 421)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 9.96 (1H, s), 7.72-7.53 (3H, m),7.46-7.41 (1H, m), 6.54 (1H, s). Melting point (° C.): 188-192.

EXAMPLE 1431-{3-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}-ethanone(CompoundNo. 422)

Melting point (° C.): 195-198.

EXAMPLE 144 Methyl 3-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]-benzoate(Compound No. 423)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 8.00-7.70 (2H, m), 7.70-7.30 (2H, m), 6.75(1H, s), 3.30 (3H, s). Melting point (° C.): 207.

EXAMPLE 145 6-Chloro-3-(3-nitrophenoxy)-4-pyridazinol (Compound No. 424)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 8.30-7.90 (2H, m), 7.90-7.70 (2H, m),6.50 (1H, s), 5.80-5.15 (1H, brs). Melting point (° C.): 217-219.

EXAMPLE 146 6-Chloro-3-(3-methoxyphenoxy)-4-pyridazinol (Compound No.425)

¹H-NMR (60 MHz, CDCl₃+DMF-d₇) δ ppm: 7.50-7.10 (1H, m), 6.90-6.60 (3H,m), 6.70 (1H, s), 5.88 (1H, brs), 3.77Melting point (° C.): 199-203.

EXAMPLE 147 6-Chloro-3-(4-chlorophenoxy)-4-pyridazinol (Compound No.427).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.45-7.38 (2H, m), 7.23-7.15 (2H, m),6.70 (1H, s). Melting point (° C.): 226-231.

EXAMPLE 148 6-Chloro-3-(4-methylphenoxy)-4-pyridazinol (Compound No.430)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 7.25-6.83 (4H, m), 6.68 (1H, s), 2.25.(3H, s). Melting point (° C.): 261-263.

EXAMPLE 149 6-Chloro-3-(4-isopropylphenoxy)-4-pyridazinol (Compound No.432)

Melting point (° C.): 233-235.

EXAMPLE 150 3-(4-tert-Butylphenoxy)-6-chloro-4-pyridazinol (Compound No.433)

Melting point (° C.): 224-225.

EXAMPLE 151 6-Chloro-3-(4-cyclopropylphenoxy)-4-pyridazinol (CompoundNo. 434)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.15-7.02 (4H, m), 6.82 (1H, brs),2.01-1.90 (1H, m), 0.99-0.90 (2H, m), 0.70-0.62 (2H, m) Melting point (°C.): 221-227.

EXAMPLE 152 6-Chloro-3-(4-methoxyphenoxy)-4-pyridazinol (Compound No.435)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.26-6.85 (4H, m), 6.80 (1H, brs), 3.81(3H, s). Melting point (° C.): 260-263.5.

EXAMPLE 153 6-Chloro-3-[4-(trimethylsilyl)phenoxy]-4-pyridazinol(Compound No. 436)

Melting point (° C.): 197-199.

EXAMPLE 154 6-Chloro-3-(2,3-difluorophenoxy)-4-pyridazinol (Compound No.437)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.24-7.05 (3H, m), 6.73 (1H, s). Meltingpoint. (C): 188-193.

EXAMPLE 155 6-Chloro-3-(3-chloro-2-fluorophenoxy)-4-pyridazinol(Compound No. 438)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.43-7.21 (3H, m), 6.75 (1H, s). Meltingpoint (° C.): 187-195.

EXAMPLE 1566-Chloro-3-[2-fluoro-3-(trifluoromethyl)phenoxy]-4-pyridazinol (CompoundNo. 441)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.78-7.66 (2H, m), 7.48 (1H, t, J=8.1Hz), 6.83 (1H, s). Melting point (° C.): 185-189.

EXAMPLE 157 6-Chloro-3-(2,3-dichlorophenoxy)-4-pyridazinol (Compound No.443)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.62-7.57 (1H, m), 7.50-7.37 (2H, m),6.89 (1H, s). Melting point (° C.): 233-238.

EXAMPLE 1586-Chloro-3-[2-chloro-3-(trifluoromethyl)phenoxy]-4-pyridazinol (CompoundNo. 446)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.74-7.55 (3H, m), 6.76 (1H, s). Meltingpoint (° C.): 170-200.

EXAMPLE 159 3-(2-Bromo-3-methylphenoxy)-6-chloro-4-pyridazinol (CompoundNo. 450)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.35 (1H, t, J=7.5 Hz), 7.27 (1H, dd,J=7.5, 2.2 Hz), 7.16 (1H, dd, J=7.5, 2.2 Hz), 6.87 (1H, brs), 2.41 (3H,s). Melting point (° C.): 140-141.

EXAMPLE 160 6-Chloro-3-(3-fluoro-2-methylphenoxy)-4-pyridazinol(Compound No. 453)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.30-7.15 (1H, m), 7.08-6.85 (2H, m),6.73 (1H, s), 2.09 (3H, d, J=1.8 Hz). Melting point (° C.): 242-244.

EXAMPLE 161 6-Chloro-3-(3-chloro-2-methylphenoxy)-4-pyridazinol(Compound No. 454)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.39-7.12 (4H, m), 2.14 (3H, s).Melting point (° C.): 250-252.

EXAMPLE 162 6-Chloro-3-(2,3-dimethylphenoxy)-4-pyridazinol (Compound No.456)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 7.22-6.98 (3H, m), 6.77 (1H, s), 2.30(3H, s), 2.02 (3H, s). Melting point (° C.): 240-241.

EXAMPLE 163 6-Chloro-3-(2-methyl-3-nitrophenoxy)-4-pyridazinol (CompoundNo. 458)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.89-7.84 (1H, m), 7.58-7.47 (2H, m),6.90 (1H, brs), 2.25 (3H, s). Melting point (° C.): 241-244.

EXAMPLE 164 6-Chloro-3-(3-methoxy-2-methylphenoxy)-4-pyridazinol(Compound No. 459)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.14 (1H, t, J=8.4 Hz), 6.78 (1H, d,J=8.4 Hz), 6.63 (1H, d, J=8.4 Hz), 6.55 (1H, s), 3.83 (3H, s), 2.00 (3H,s). Melting point (° C.): 224-237.

EXAMPLE 1656-Chloro-3-{3-[(6-chloro-4-hydroxy-3-pyridazinyl)-oxy]-2-methylphenoxy}-4-pyridazinol(Compound No. 460)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.16 (1H, t, J=8.4 Hz), 6.85 (2H, d,J=8.4 Hz), 6.48 (2H, s), 2.15 (3H, s). Melting point (° C.): >290.

EXAMPLE 166 6-Chloro-3-(2-cyclopropyl-3-methylphenoxy)-4-pyridazinol(Compound No. 472)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.18 (1H, t, J=7.7 Hz), 7.07 -(1H,br.d, J=7.7 Hz), 6.91 (1H, br.d, J=7.7 Hz), 6.82 (1H, brs), 2.40 (3H,s), 1.43-1.28 (1H, m), 0.79-0.68 (2H, m), 0.59-0.48 (2H, m). Meltingpoint (° C.): 197-198.

EXAMPLE 167 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyltetrahydro-2H-pyran-4-carboxylate (Compound No. 3856)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.38 (1H, s), 7.15-7.04 (2H, m),6.90-6.78 (1H, m), 4.10-3.95 (2H, m), 3.60-3.43 (2H, m), 3.03-2.86 (1H,m), 2.11 (3H, s), 2.06-1.90 (4H, m), 1.80-1.60 (1H, m), 0.80-0.50 (4H,m). Appareance: caramel-like.

EXAMPLE 168 Methyl2-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]-6-fluorobenzoate (Compound No.491)

¹H-NMR (270 MHz, CDCl₃) δ ppm: 7.62 (1H, td, J=8.4, 5.6 Hz), 7.23 (1H,t, J=8.4 Hz), 7.02 (1H, d, J=8.4 Hz), 3.83 (3H, s). Appareance:amorphous.

EXAMPLE 169 6-Chloro-3-(3-methyl-2-nitrophenoxy)-4-pyridazinol (CompoundNo. 498)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.48 (1H, t, J=8.1 Hz), 7.26 (1H, d,J=8.1 Hz), 7.19 (1H, d, J=8.1 Hz), 6.66 (1H, s), 2.37 (3H, s). Meltingpoint (° C.): 191-200.

EXAMPLE 170 6-Chloro-3-(2,3-dimethoxyphenoxy)-4-pyridazinol (CompoundNo. 503)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.14-6.78 (4H, m), 3.84 (3H, s), 3.61(3H, s). Melting point (° C.): 199-201.

EXAMPLE 171 6-Chloro-3-(2,3-dihydro-1H-inden-4-yloxy)-4-pyridazinol(Compound No. 506)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.20 (1H, t, J=7.3 Hz), 7.14 (1H, d,J=7.3 Hz), 6.92 (1H, d, J=7.3 Hz), 6.83 (1H, brs), 2.92 (1H, t, J=7.3Hz), 2.64 (1H, t, J=7.3 Hz), 2.00 (1H, quintet, J=7.3 Hz). Melting point(° C.): 230-232.

EXAMPLE 1726-Chloro-3-[(3-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-4-pyridazinol(Compound No. 507)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.17 (1H, t, J=7.7 Hz), 7.08 (1H, d,J=7.7 Hz), 6.88 (1H, d, J=7.7 Hz), 6.69 (1H, s), 3.35-3.15 (1H, m),3.10-2.70 (2H, m), 2.40-2.15 (1H, m), 1.80-1.55 (1H, m), 1.15 (3H, d,J=7.0 Hz). Melting point (° C.): 232.

EXAMPLE 1736-Chloro-3-[(1-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-4-pyridazinol(Compound No. 510)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.21 (1H, dd, J=8.1, 7.3 Hz) 7.09 (1H, d,J=7.3 Hz), 6.91 (1H, d, J=8.1 Hz), 6.70 (1H, s), 3.30-3.05 (1H, m),2.85-2.50 (2H, m), 2.40-2.20 (1H, m), 1.70-1.45 (1H, m), 1.29 (3H, d,J=7.0 Hz). Melting point (° C.): 228-230.

EXAMPLE 1746-Chloro-3-[(2,2-dimethyl-2,3-dihydro-1H-inden-4-yl)oxy]-4-pyridazinol(Compound No. 513)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.17 (1H, t, J=7.7 Hz), 7.05 (1H, d,J=7.7 Hz), 6.89 (1H, d, J=7.7 Hz), 6.69 (1H, s), 2.76 (2H, s), 2.53 (2H,s), 1.13 (6H, s). Melting point (° C.): 220-223.

EXAMPLE 1756-Chloro-3-{spiro[cyclopropane-1,3′-(2′,3′-dihydro-1′H-inden)]-4′-yloxy}-4-pyridazinol(Compound No. 514)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.15-6.95 (2H, m), 6.75 (1H, dd, J=6.6,2.6 Hz), 6.66 (1H, s), 3.02 (2H, dd, J=7.7, 7.3 Hz), 2.15-1.95 (2H, m),1.28-1.15 (2H, m), 0.80-0.70 (2H, m) Appareance: amorphous.

EXAMPLE 176 6-Chloro-3-(4-fluorophenoxy)-4-pyridazinol (Compound No.426)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.26-7.05 (4H, m), 6.70 (1H, s). Meltingpoint (° C.): 241-248.

EXAMPLE 1773-(Bicyclo[4.2.0]octa-1,3,5-trien-2-yloxy)-6-chloro-4-pyridazinol(Compound No. 505)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.22 (1H, dd, J=8.2, 7.3 Hz), 6.96 (1H,d, J=8.2 Hz), 6.91 (1H, d, J=7.3 Hz), 6.69 (1H, s), 3.19-3.11 (2H, m),3.10-3.00 (2H, m). Melting point (° C.): 145-155.

EXAMPLE 1787-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-2,3-dihydro-1H-inden-1-one0-methyloxime (Compound No. 520)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.50-7.15 (2H, m), 7.07 (1H, dd, J=8.1,7.3 Hz), 6.55 (0.4H, s), 5.77 (0.6H, s), 3.73 (1.8H, s), 3.67 (1.2H, s),3.15-3.00 (2H, m), 2.90-2.73 (2H, m). Melting point (° C.): >250.

EXAMPLE 1796-Chloro-3-(5,6,7,8-tetrahydro-1-naphthalenyloxy)-4-pyridazinol(Compound No. 521)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.14 (1H, t, J=7.7 Hz), 6.98 (1H, d,J=7.7 Hz), 6.89 (1H, d, J=7.7 Hz), 6.82 (1H, brs), 2.80-2.70 (2H, m),2.50-2.40 (2H, m), 1.85-1.70 (4H, m).

Melting point. (C): 232-237.

EXAMPLE 180 6-Chloro-3-(1-naphthyloxy)-4-pyridazinol (Compound No. 527)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 8.10-7.20 (7H, m), 6.85 (1H, s), 6.20(1H, brs). Melting point (° C.): 243-245.

EXAMPLE 181 6-Chloro-3-(2,3-dihydro-1-benzofuran-4-yloxy)-4-pyridazinol(Compound No. 528)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.11 (1H, t, J=8.1 Hz), 6.65 (1H, s),6.60 (1H, d, J=8.1 Hz), 6.56 (1H d, J=8.1 Hz), 4.53 (2H, t, J=8.5 Hz),2.97 (2H, t, J=8.5 Hz). Melting point (° C.): 219-221.

EXAMPLE 1826-Chloro-3-[(3-methyl-2,3-dihydro-1-benzofuran-4-yl)oxy]-4-pyridazinol(Compound No. 529)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.15 (1H, t, J=8.1 Hz), 6.85 (1H, brs),6.67 (1H, d, J=8.1 Hz), 6.62 (1H, d, J=8.1 Hz), 4.65 (1H, t, J=8.8 Hz),4.12-4.04 (1H, m), 3.50-3.39 (1H, m), 1.14 (3H, d, J=7.0 Hz). Meltingpoint (° C.): 238-245.

EXAMPLE 183 3-(1-benzofuran-4-yloxy)-6-chloro-4-pyridazinol (CompoundNo. 531)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.99 (1H, d, J=2.0 Hz), 7.52 20 (1H, d,J=7.8 Hz), 7.35 (1H, t, J=7.8 Hz), 7.06 (1H, d, J=7.8 Hz), 6.87 (1H, s),6.81 (1H, d, J=2.0 Hz). Melting point (° C.): 220-225.

EXAMPLE 184 6-Chloro-3-[(3-methyl-1-benzofuran-4-yl)oxy]-4-pyridazinol(Compound No. 532)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.44 (1H, d, J=1.5 Hz), 7.33-7.20 (2H,m), 6.91 (1H, dd, J=7.0, 1.5 Hz), 6.61 (1H, s), 2.01 (3H, s). Meltingpoint (° C.): 218-225.

EXAMPLE 185 3-(1-Benzothien-4-yloxy)-6-chloro-4-pyridazinol (CompoundNo. 534)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.75 (1H, d, J=8.1 Hz), 7.53 (1H, d,J=5.5 Hz), 7.35 (1H, dd, J=8.1, 7.7 Hz), 7.28 (1H, 35 dd, J=5.5, 0.7Hz), 7.10 (1H, dd, J=7.7, 0.7 Hz), 6.64 (1H, s). Melting point (° C.):181-183.

EXAMPLE 186 6-Chloro-3-(8-quinolynyloxy)-4-pyridazinol (Compound No.535)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 8.80 (1H, dd, J=4.0, 1.5 Hz), 8.46 (1H,dd, J=8.4, 1.5 Hz), 7.93-7.87 (1H, m), 7.70-7.63 (2H, m), 7.57 (1H, dd,J=8.4, 4.0 Hz), 6.82 (1H, s). Melting point (° C.): >200 (dec.).

EXAMPLE 187 6-Chloro-3-(8-quinolynyloxy)-4-pyridazinol (Compound No.536)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 8.81 (1H, dd, J=4.0, 1.5 Hz), 8.41 (1H,dd, J=8.4, 1.5 Hz), 7.81 (1H, d, J=7.0 Hz), 7.62-7.52 (2H, m), 7.41 (1H,d, J=7.7 Hz), 6.43 (1H, s). Melting point (° C.): >180 (dec.).

EXAMPLE 188 6-Chloro-3-[(2-methyl-1,3-benzoxazol-4-yl)oxy]-4-pyridazinol(Compound No. 538)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.55-7.32 (2H, m), 7.22-7.10 (1H, m),6.73 (1H, s), 2.59 (3H, s). Melting point (° C.): 221-222.

EXAMPLE 189 6-Chloro-3-(2,3-dihydro-1-benzofuran-7-yloxy)-4-pyridazinol(Compound No. 539)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.13-7.08 (1H, m), 6.95 (1H, d, J=7.3Hz), 6.85 (1H, dd, J=8.1, 7.3 Hz), 6.67 (1H, s), 4.54 (2H, t, J=8.4 Hz),3.30-3.20 (2H, m). Appareance: amorphous.

EXAMPLE 1906-Chloro-3-[(2,2-dimethyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-4-pyridazinol(Compound No. 540)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.08 (1H, d, J=7.3 Hz), 6.96 (1H, d,J=8.1 Hz), 6.87-6.79 (2H, m), 3.06 (2H, s), 1.37 (6H, s). Melting point(° C.): 228-229.5.

EXAMPLE 191 3-(1-Benzofuran-7-yloxy)-6-chloro-4-pyridazinol (CompoundNo. 541)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.73 (1H, d, J=2.2 Hz), 7.53 (1H, dd,J=7.7, 1.4 Hz), 7.26 (1H, t, J=7.7 Hz), 7.15 (1H, dd, J=7.7, 1.4 Hz),6.90 (1H, d, J=2.2 Hz), 6.76 (1H, s). Melting point (° C.): 201-202.

EXAMPLE 192 3-(1,3-Benzodioxol-4-yloxy)-6-chloro-4-pyridazinol (CompoundNo. 544)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 6.94-6.75 (4H, m), 6.01 (2H, s).Melting point (° C.): 206-211.

EXAMPLE 1936-Chloro-3-(2,3-dihydro-1,4-benzodioxyn-5-yloxy)-4-pyridazinol (CompoundNo. 547)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 6.90-6.72 (4H, m), 4.27-4.15 (4H, m).Melting point (° C.): 218-223.5.

EXAMPLE 194 6-Chloro-3-[(2-methyl-1,3-benzoxazol-7-yl)oxy]-4-pyridazinol(Compound No. 549)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.52 (1H, dd, J=8.1, 1.1 Hz) 7.37 (1H, t,J=8.1 Hz), 7.21 (1H, dd, J=8.1, 1.1 Hz), 6.76 (1H, s), 2.65 (3H, s).Melting point (° C.): 197-202.

EXAMPLE 195 6-Chloro-3-(2,4-dichlorophenoxy)-4-pyridazinol (Compound No.552)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.55 (1H, t, J=1.8 Hz), 7.35 (2H, d,J=1.8 Hz), 6.88 (1H, s). Melting point (° C.): 233-237.

EXAMPLE 196 3-(2-Bromo-4-tert-butylphenoxy)-6-chloro-4-pyridazinol(Compound No. 556)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 7.61 (1H, d, J=2.0 Hz), 7.43 (1H, dd,J=8.4, 2.0 Hz), 7.17 (1H, d, J=8.4 Hz), 6.73 (1H, s), 1.32 (9H, s).Melting point (° C.): >202 (dec.).

EXAMPLE 197 6-Chloro-3-(4-chloro-2-methylphenoxy)-4-pyridazinol(Compound No. 558)

¹H-NMR (60 MHz, DMSO-d₆+CDCl₃) δ ppm: 7.40-7.10 (3H, m), 6.65 (1H, s),2.18 (3H, s). Melting point (° C.): 235-235.5.

EXAMPLE 198 6-Chloro-3-(2,4-dimethylphenoxy)-4-pyridazinol (Compound No.559)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.17-6.98 (3H, m), 6.85 (1H, s), 2.29 (3H,s), 2.07 (3H, s). Melting point (° C.): 217.5.

EXAMPLE 199 6-Chloro-3-(2-ethyl-4-iodophenoxy)-4-pyridazinol (CompoundNo. 562)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.59 (1H, d, J=2.2 Hz), 7.49 (1H, dd,J=8.4, 2.2 Hz), 6.75 (1H, d, J=8.4 Hz), 6.48 (1H, s), 2.65-1.95 (2H, m),1.16 (3H, t, J=7.7 Hz). Melting point (° C.): 199-201.

EXAMPLE 200 3-(4-Bromo-2-isopropylphenoxy)-6-chloro-4-pyridazinol(Compound No. 566)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 7.44 (1H, brs), 7.37 (1H, dd, J=8.0, 2.2Hz), 7.00 (1H, d, J=8.0 Hz), 6.73 (1H, s), 3.01 (1H, septet, J=6.8 Hz),1.15 (6H, d, J=6.8 Hz). Melting point (° C.): 215-225.

EXAMPLE 201 3-(2-tert-Butyl-4-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 567)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.25 (1H, d, J=2.0 Hz), 7.05 (1H, dd,J=8.0, 2.0 Hz), 6.85 (1H, d, J=8.0 Hz), 6.70 (1H, s), 2.30 (3H, s), 1.35(9H, s). Melting point (° C.): 230-236.

EXAMPLE 202 6-Chloro-3-(2-cyclopropyl-4-methylphenoxy)-4-pyridazinol(Compound No. 571)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.05-6.95 (1H, m), 6.96 (1H, s), 6.81(1H, s), 6.68 (1H, m), 2.30 (3H, s), 1.90-1.75 (1H, m), 0.90-0.70 (2H,m), 0.70-0.50 (2H, m). Melting point (IC): 239.

EXAMPLE 203 6-Chloro-3-(2-chloro-5-methylphenoxy)-4-pyridazinol(Compound No. 614)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.40 (1H, d, J=8.5 Hz), 7.15 (1H, s), 7.10(1H, d, J=8.5 Hz), 6.70 (1H, s), 2.35 (3H, s). Melting point (° C.):170.

EXAMPLE 204 6-Chloro-3-(5-chloro-2-methylphenoxy)-4-pyridazinol(Compound No. 618)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.28 (1H, d, J=8.8 Hz), 7.21-7.15 (1H,m), 7.16 (1H, s), 6.72 (1H, s), 2.15 (3H, Melting point (° C.): 174-180.

EXAMPLE 205 6-Chloro-3-(2,5-dimethylphenoxy)-4-pyridazinol (Compound No.621)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.16 (1H, d, J=9.0 Hz), 7.08 (1H, d, J=9.0Hz), 6.90 (1H, s), 6.70 (1H, s), 2.30 (3H, s) 2.10 (3H, s). Meltingpoint (° C.): 80-83.

EXAMPLE 206 6-Chloro-3-(5-isopropyl-2-methylphenoxy)-4-pyridazinol(Compound No. 623)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.20 (1H, d, J=7.5 Hz), 7.15-6.98 (1H, m),6.95 (1H, s), 6.70 (1H, s), 2.88 (1H, s J=7.5 Hz), 2.10 (3H, s), 1.23(6H, d, J=7.5 Hz). Melting point (° C.): 168-169.

EXAMPLE 207 3-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-4-methylbenzoicacid (Compound No. 626) Melting point (° C.): 238-240. EXAMPLE 2083-(5-Amino-2-methylphenoxy)-6-chloro-4-pyridazinol (Compound No. 627)Melting point (° C.): >310. EXAMPLE 2096-Chloro-3-[5-(dimethylamino)-2-methylphenoxy]-4-pyridazinol (CompoundNo. 628)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.08 (1H, d, J=8.4 Hz), 6.68 (1H, s),6.61 (1H, dd, J=8.4, 2.6 Hz), 6.50 (1H, d, J=2.6 Hz), 2.88 (6H, s), 2.02(3H, s). Melting point (° C.): 181-182.

EXAMPLE 210 6-Chloro-3-(5-methoxy-2-methylphenoxy)-4-pyridazinol(Compound No. 629)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.16 (1H, d, J=8.4 Hz), 6.78-6.67 (3H,m), 3.75 (3H, s), 2.07 (3H, s). Melting point (° C.): 170-172.

EXAMPLE 211 6-Chloro-3-(2-ethyl-5-methoxyphenoxy)-4-pyridazinol(Compound No. 635)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.15 (1H, br.d, J=8.0 Hz), 6.74 (1H,brs), 6.73 (1H, br.d, J=8.0 Hz), 6.63 (1H, s), 3.73 (3H, s), 2.46 (2H,q, J=7.0 Hz), 1.10 (3H, t, J=7.0 Hz). Melting point (° C.): 124-126.

EXAMPLE 212 6-Chloro-3-(2-isopropyl-5-methylphenoxy)-4-pyridazinol(Compound No. 640)

¹H-NMR (60 MHz, CDCl₃+DMF-d₇) δ ppm: 7.50-6.70 (3H, m), 6.58 (1H, s),3.30-2.60 (1H, m), 2.26 (3H, s), 1.13 (6H, d, J=6.60 Hz). Melting point(° C.): 193-195.

EXAMPLE 213 6-Chloro-3-(3,5-diisopropylphenoxy)-4-pyridazinol (CompoundNo. 642)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 7.25 (1H, d, J=8.0 Hz), 7.11 (1H, d,J=1.8 Hz), 6.92 (1H, dd, J=8.0, 1.8 Hz), 6.73 (1H, s), 2.84 (2H, septet,J=7.0 Hz), 1.18 (6H, d, J=7.0 Hz), 1.12 (6H, d, J=7.0 Hz). Melting point(° C.): 231-235.

EXAMPLE 214 3-(2-tert-Butyl-5-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 650)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.35 (1H, d, J=8.0 Hz), 6.95 (1H, dd,J=8.0, 1.5 Hz), 6.80 (1H, s), 6.70 (1H, s), 2.27 (3H, s), 1.35 (9H, s).Melting point (° C.): 226.

EXAMPLE 215 6-Chloro-3-(2,5-di-tert-butylphenoxy)-4-pyridazinol(Compound No. 653)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.50-7.10 (3H, m), 6.94 (1H, s), 4.98 (1Hbrs), 1.37 (9H, s), 1.28 (9H, s). Melting point (° C.): 249-258.

EXAMPLE 216 6-Chloro-3-(2-cyclopropyl-5-fluorophenoxy)-4-pyridazinol(Compound No. 658)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.10-6.85 (3H, m), 6.72 (1H, s),1.92-1.75 (1H, m), 0.85-0.70 (2H, m), 0.70-0.54 (2H, m). Melting point(° C.): 227-228.

EXAMPLE 217 6-Chloro-3-(5-chloro-2-cyclopropylphenoxy)-4-pyridazinol(Compound No. 659)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.19 (1H, d, J=7.7 Hz), 7.16 (1H, s),7.01 (1H, d, J=7.7 Hz), 6.72 (1H, s), 1.94-1.79 (1H, m), 0.90-0.75 (2H,m), 0.75-0.58 (2H, m). Melting point (° C.): 194-195.

EXAMPLE 218 6-Chloro-3-(2-cyclopropyl-5-methylphenoxy)-4-pyridazinol(Compound No. 662)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.96 (1H, d, J=7.7 Hz), 6.89 (1H, s),6.87 (1H, d, J=7.7 Hz), 6.68 (1H, s), 2.28 (3H, s), 1.87-1.73 (1H, m),0.80-0.51 (4H, m) Melting point (° C.): 150-159.

EXAMPLE 219 6-Chloro-3-(2-cyclopropyl-5-ethylphenoxy)-4-pyridazinol(Compound No. 663)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.01 (1H, d, J=8.0 Hz), 6.92 (1H, s),6.92 (1H, d, J=8.0 Hz), 6.69 (1H, s), 2.61 (2H, t, J=7.7 Hz), 1.88-1.72(1H, m), 1.20 (3H, q, J=7.7 Hz), 0.82-0.66 (2H, m), 0.65-0.52 (2H, m).Appareance: amorphous.

EXAMPLE 220 6-Chloro-3-(2-cyclopropyl-5-isopropylphenoxy)-4-pyridazinol(Compound No. 664)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.05 (1H, dd, J=7.7, 1.8 Hz), 7.00 (1H,brs), 6.93 (1H, d, J=7.7 Hz), 6.70 (1H, s), 2.87 (1H, septet, J=7.0 Hz),1.90-1.72 (1H, m), 1.22 (6H, d, J=7.0 Hz), 0.85-0.68 (2H, m), 0.68-0.52(2H, m). Melting point (° C.): 211-212.

EXAMPLE 2213-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-4-cyclopropylbenzonitrile(Compound No. 667)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.58-7.48 (2H, m), 7.15 (1H, d, J=8.8Hz), 6.74 (1H, s), 2.10-1.90 (1H, m), 1.05-0.93 (2H, m), 0.83-0.70 (2H,m). Melting point (° C.): 211-212.

EXAMPLE 222 6-Chloro-3-[5-fluoro-2-(1-propenyl)phenoxy]-4-pyridazinol(Compound No. 679)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.61-7.53 (1H, m), 7.03-6.90 (2H, m),6.72 (1H, s), 6.44-6.19 (2H, m), 1.80 (3H, d, J=5.5 Hz). Melting point(° C.): 210-217.

EXAMPLE 223 6-Chloro-3-[5-chloro-2-(1-propenyl)phenoxy]-4-pyridazinol(Compound No. 680)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.55 (1H, d, J=8.4 Hz), 7.24-7.17 (2H,m), 6.72 (1H, s), 6.46-6.30 (2H, m), 1.81 (3H, d, J=5.1 Hz). Meltingpoint (° C.): 221-224.

EXAMPLE 2242-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-4-(dimethylamino)benzaldehyde(Compound No. 692)

¹H-NMR (90 MHz, DMSO-d₆) δ ppm: 9.78 (1H, s), 7.69 (1H, d, J=6.0 Hz),6.81 (1H, s), 6.78-6.46 (2H, m), 3.05 (6H, s). Melting point (° C.):124-127.

EXAMPLE 225 3-(5-Chloro-2-methoxyphenoxy)-6-chloro-4-pyridazinol(Compound No. 701)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.23-7.18 (2H, m), 7.05 (1H, d, J=8.8Hz), 6.66 (1H, s), 3.73 (3H, s). Melting point (° C.): 143-155.

EXAMPLE 226 3-(5-Bromo-2-methoxyphenoxy)-6-chloro-4-pyridazinol(Compound No. 702)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.39-7.31 (2H, m), 7.02 (1H, d, J=8.4Hz), 6.67 (1H, s), 3.74 (3H, s). Melting point (° C.): 135-137.

EXAMPLE 227 6-Chloro-3-(4-fluoro-2-methylphenoxy)-4-pyridazinol(Compound No. 557)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.14-6.88 (3H, m), 6.71 (1H, s), 2.16(3H, s). Melting point (° C.): 249-250.

EXAMPLE 2283-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-4-methoxybenzonitrile(Compound No. 707)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.66 (1H, dd, J=8.4, 2.2 Hz), 7.58 (1H,d, J=2.2 Hz), 7.26 (1H, d, J=8.4 Hz), 6.71 (1H, s), 3.85 (3H, s).Melting point (° C.): 187-192.

EXAMPLE 229 6-Chloro-3-(2-methoxy-5-nitrophenoxy)-4-pyridazinol(Compound No. 708)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.18 (1H, dd, J=9.2, 2.6 Hz) 8.04 (1H, d,J=2.6 Hz), 7.27 (1H, d, J=9.2 Hz), 6.59 (1H, s), 3.89 (3H, s).Appareance: amorphous.

EXAMPLE 230 6-Chloro-3-(2,5-dimethoxyphenoxy)-4-pyridazinol (CompoundNo. 709)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.04-6.99 (1H, m), 6.81-6.78 (2H, m),6.68 (1H, s), 3.76 (3H, s), 3.70 (3H, s). Melting point (° C.): 150-152.

EXAMPLE 231 6-Chloro-3-(2,6-difluorophenoxy)-4-pyridazinol (Compound No.710)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.54-7.20 (3H, m), 6.88 (1H, s).Melting point (° C.): 209-213.

EXAMPLE 232 6-Chloro-3-(2-chloro-6-fluorophenoxy)-4-pyridazinol(Compound No. 711)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.35-7.13 (3H, m), 6.61 (1H, s). Meltingpoint (° C.): 235.

EXAMPLE 233 3-(2-Bromo-6-fluorophenoxy)-6-chloro-4-pyridazinol (CompoundNo. 712)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.31-7.15 (3H, m), 6.65 (1H, s).Appareance: amorphous.

EXAMPLE 234 6-Chloro-3-(2-fluoro-6-propylphenoxy)-4-pyridazinol(Compound No. 716) Melting point (° C.): 134-137. EXAMPLE 2356-Chloro-3-(2-fluoro-6-isopropylphenoxy)-4-pyridazinol (Compound No.717)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.35-7.15 (3H, m), 6.89 (1H, brs), 3.02(1H, septet, J=7.0 Hz), 1.14 (6H, J=7.0 Hz). Melting point (° C.):215-220.

EXAMPLE 236 6-Chloro-3-(2-cyclopropyl-6-fluorophenoxy)-4-pyridazinol(Compound No. 719)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.22-6.96 (2H, m), 6.81-6.71 (1H, m),6.72 (1H, s), 2.03-1.89 (1H, m), 0.93-0.80 (2H, m), 0.69-0.62 (2H, m).Melting point (° C.): 200-203.

EXAMPLE 2376-Chloro-3-{2-[1-(ethylsulfanyl)ethyl]-6-fluorophenoxy}-4-pyridazinol(Compound No. 728)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.42 (1H, d, J=8.1 Hz), 7.26-7.15 (1H,m), 7.07-6.97 (1H, m), 6.46 (1H, s), 4.33 (1H, q, J=7.0 Hz), 2.42-2.20(2H, m), 1.43 (3H, d, J=7.0 Hz), 1.02 (3H, t, J=7. 0 Hz) Physicalproperty: amorphous.

EXAMPLE 238 6-Chloro-3-(2-fluoro-6-nitrophenoxy)-4-pyridazinol (CompoundNo. 731)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.03-7.99 (1H, m), 7.78-7.53 (2H, m),6.89 (1H, s) Melting point (° C.): 210 (sublimation).

EXAMPLE 239 6-Chloro-3-(2-fluoro-6-methoxyphenoxy)-4-pyridazinol(Compound No. 732)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.26 (1H, dd, J=15.0, 8.1 Hz),7.02-6.91 (2H, m), 6.84 (1H, s), 3.75 (3H, s). Melting point (° C.):190-194 (sublimation).

EXAMPLE 240 6-Chloro-3-(2,6-dichlorophenoxy)-4-pyridazinol (Compound No.733)

¹H-NMR (90 MHz, DMSO-d₆) δ ppm: 7.70-7.10 (3H, m), 6.80 (1H, s). Meltingpoint (° C.): 265.

EXAMPLE 241 6-Chloro-3-(2-chloro-6-iodophenoxy)-4-pyridazinol (CompoundNo. 735)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.90 (1H, d, J=8.1 Hz), 7.64 (1H, d,J=8.1 Hz), 7.12 (1H, t, J=8.1 Hz), 7.02-6.80 (1H, br.m). Melting point(° C.): 262-264.

EXAMPLE 242 6-Chloro-3-(2-chloro-6-methylphenoxy)-4-pyridazinol(Compound No. 736)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.50-7.00 (3H, m), 6.75 (1H, s), 2.22 (3H,s). Melting point (° C.): 235.

EXAMPLE 243 6-Chloro-3-(2-chloro-6-ethylphenoxy)-4-pyridazinol (CompoundNo. 737)

Melting point (° C.): 194-195.

EXAMPLE 244 6-Chloro-3-(5-fluoro-2-methoxyphenoxy)-4-pyridazinol(Compound No. 700)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.13-6.94 (3H, m), 6.71 (1H, s), 3.74(1H, s). Melting point (° C.): 187-191.

EXAMPLE 245 6-Chloro-3-(2-chloro-6-cyclopropylphenoxy)-4-pyridazinol(Compound No. 740)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.30 (1H, dd, J=8.1, 1.5 Hz), 7.17 (1H,dd, J=8.1, 7.7 Hz), 6.96 (1H, dd, J=7.7, 1.5 Hz), 6.76 (1H, s),2.00-1.84 (1H, m), 0.95-0.80 (2H, m), 0.70-0.60 (2H, m). Melting point(° C.): 224-225.

EXAMPLE 2466-Chloro-3-[2-chloro-6-(2-methyl-2-propenyl)phenoxy]-4-pyridazinol(Compound No. 746)

Melting point (° C.): 198-200.

EXAMPLE 247 6-Chloro-3-(2-chloro-6-nitrophenoxy)-4-pyridazinol (CompoundNo. 754)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.12 (1H, dd, J=8.1, 1.5 Hz), 7.95 (1H,dd, J=8.1, 1.5 Hz), 7.59 (1H, t, J=8.1 Hz), 6.76 (1H, s). Appearance:amorphous.

EXAMPLE 248 6-Chloro-3-(2,6-dibromophenoxy)-4-pyridazinol (Compound No.756)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.65 (2H, d, J=8.1 Hz), 7.11 (1H, t,J=8.1 Hz), 6.74 (1H, brs). Melting point (° C.): 274-278.

EXAMPLE 249 3-(2-Bromo-6-methylphenoxy)-6-chloro-4-pyridazinol (CompoundNo. 758)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.56 (1H, br.d, J=7.7 Hz) 7.36 (1H,br.d, J=7.7 Hz), 7.16 (1H, t, J=7.7 Hz), 6.92 (1H, brs), 2.14 (3H, s).Melting point (° C.): 242-243.

EXAMPLE 250 3-(2-Bromo-6-ethylphenoxy)-6-chloro-4-pyridazinol (CompoundNo. 759)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.49 (1H, dd, J=7.9, 1.6 Hz), 7.32 (1H,dd, J=7.9, 1.6 Hz), 7.14 (1H, t, J=7.9 Hz), 6.75 (1H, s), 2.58 (2H, q,J=7.5 Hz), 1.18 (3H, t, J=7.5 Hz). Melting point (° C.): 215-217.

EXAMPLE 2513-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-4-methoxybenzonitrile(Compound No. 707)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.66 (1H, dd, J=8.4, 2.2 Hz), 7.58 (1H,d, J=2.2 Hz), 7.26 (1H, d, J=8.4 Hz), 6.71 (1H, s), 3.85 (3H, s).Melting point (° C.): 187-192.

EXAMPLE 252 3-(2-Bromo-6-chlorophenoxy)-6-chloro-4-pyridazinol (CompoundNo. 734)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.64 (1H, dd, J=1.5 Hz, 8.1 Hz), 7.52(1H, dd, J=1.5 Hz, 8.0 Hz), 7.21 (1H, t, J=8.1 Hz), 6.76 (1H, s).Melting point (° C.): 266-274.

EXAMPLE 253 3-(2-Bromo-6-cyclopropylphenoxy)-6-chloro-4-pyridazinol(Compound No. 762)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.51 (1H, d, J=7.8 Hz), 7.14 (1H, t,J=7.8 Hz), 7.02 (1H, d, J=7.8 Hz), 6.89 (1H, s), 1.89-1.75 (1H, m),0.88-0.75 (2H, m), 0.75-0.58 (2H, m). Melting point (° C.): 230-232.

EXAMPLE 2543-Bromo-2-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]-benzonitrile (CompoundNo. 775)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.00 (1H, dd, J=8.1, 1.5 Hz), 7.82 (1H,dd, J=8.1, 1.5 Hz), 7.37 (1H, t, J=8.1 Hz), 6.75 (1H, s). Melting point(° C.): 188 (dec.).

EXAMPLE 255 3-(2-Bromo-6-methoxyphenoxy)-6-chloro-4-pyridazinol(Compound No. 778)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.26-7.05 (3H, m), 6.70 (1H, s), 3.78(3H, s). Melting point (° C.): 220-221.

EXAMPLE 256 6-Chloro-3-(2-iodo-6-methylphenoxy)-4-pyridazinol (CompoundNo. 780)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.70 (1H, d, J=7.7 Hz), 7.29 (1H, d,J=8.1 Hz), 6.95 (1H, t, J=7.7 Hz), 6.76 (1H, s), 2.20 (3H, s). Meltingpoint (° C.): 250-252.

EXAMPLE 257 6-Chloro-3-(2-ethyl-6-iodophenoxy)-4-pyridazinol (CompoundNo. 781)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.72 (1H, dd, J=7.7, 1.5 Hz), 7.33 (1H,dd, J=7.7, 1.5 Hz), 7.00 (1H, t, J=7.7 Hz), 6.76 (1H, s), 2.57 (2H, q,J=7.7 Hz), 1.17 (3H, t, J=7.7 Hz). Melting point (° C.): 242-244.

EXAMPLE 258 6-Chloro-3-(2-iodo-6-isopropylphenoxy)-4-pyridazinol(Compound No. 782)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.70 (1H, dd, J=8.0, 1.5 Hz) 7.40 (1H,dd, J=8.0, 1.5 Hz), 7.03 (1H, t, J=8.0 Hz), 6.76 (1H, s), 3.01 (1H,septet, J=7.0 Hz), 1.18 (6H, d, J=7.0 Hz). Melting point (° C.):250-255.

EXAMPLE 2593-Bromo-2-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]-benzonitrile (CompoundNo. 775)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.00 (1H, dd, J=8.1, 1.5 Hz), 7.82 (1H,dd, J=8.1, 1.5 Hz), 7.37 (1H, t, J=8.1 Hz), 6.75 (1H, s). Melting point(° C.): 188 (dec.).

EXAMPLE 260 6-Chloro-3-(2-ethyl-6-methylphenoxy)-4-pyridazinol (CompoundNo. 802)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.12-6.97 (3H, m), 6.52 (1H, s), 2.37(2H, q, J=7.6 Hz), 1.95 (3H, s), 1.04 (3H, t, J=7.6 Hz). Appearance:amorphous.

EXAMPLE 261 6-Chloro-3-(2-isopropyl-6-methylphenoxy)-4-pyridazinol(Compound No. 803)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.23-7.06 (3H, m), 6.72 (1H, s), 2.96(1H, septet, J=7.0 Hz), 2.10 (3H, s), 1.16 (6H, d, J=7.0 Hz). Meltingpoint (° C.): 215-220.

EXAMPLE 262 3-(2-s-Butyl-6-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 804)

Melting point (° C.): 187-189.

EXAMPLE 2636-Chloro-3-[2-(2,2-dichlorocyclopropyl)-6-methylphenoxy]-4-pyridazinol(Compound No. 827)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.25 (1H, br.d, J=6.2 Hz), 7.16 (1H, dd,J=7.7, 7.3 Hz), 6.98 (1H, br.d, J=7.7 Hz), 6.72 (1H, s), 2.85 (1H, dd,J=11.0, 10.6 Hz), 2.22 (3H, s). Melting point (° C.): 213-215.

EXAMPLE 264 6-Chloro-3-(2-methyl-6-vinylphenoxy)-4-pyridazinol (CompoundNo. 834)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.46 (1H, dd, J=6.6, 2.6 Hz), 7.25-7.05(2H, m), 6.71 (1H, dd, J=17.6, 11.4 Hz), 6.70 (1H, s), 5.74 (1H, dd,J=17.6, 1.5 Hz), 5.21 (1H, dd, J=11.4, 1.5 Hz), 2.11 (3H, s).Appearance: amorphous.

EXAMPLE 2656-Chloro-3-(6-cyclopropyl-3-fluoro-2-methylphenoxy)-4-pyridazinol(Compound No. 1052)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.92-6.70 (3H, m), 2.06 (3H, d, J=2.2Hz), 1.85-1.70 (1H, m), 0.79-0.45 (4H, m). Melting point (° C.):230-231.

EXAMPLE 266 6-Chloro-3-(2-methyl-6-nitrophenoxy)-4-pyridazinol (CompoundNo. 844)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.95 (1H, d, J=8.1 Hz), 7.76 (1H, d,J=7.7 Hz), 7.45 (1H, dd, J=8.1, 7.7 Hz), 6.80 (1H, s), 2.20 (3H, s).Appearance: paste state.

EXAMPLE 267 6-Chloro-3-(2-methoxy-6-methylphenoxy)-4-pyridazinol(Compound No. 845)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.10-7.01 (1H, m), 6.79-6.72 (2H, m),6.55 (1H, s), 3.64 (3H, s), 2.08 (3H, s). Appearance: amorphous.

EXAMPLE 268 6-Chloro-3-(2,6-diethylphenoxy)-4-pyridazinol (Compound No.846)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 10.21 (1H, brs), 7.02 (3H, brs), 6.47 (1H,s), 2.27 (4H, q, J=7.6 Hz), 0.98 (6H, t, J=7.6 Hz). Melting point (°C.): 181-185.

EXAMPLE 269 6-Chloro-3-(2-cyclopropyl-6-ethylphenoxy)-4-pyridazinol(Compound No. 850)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.11 (2H, d, J=4.8 Hz), 6.85 (1H, t,J=4.8 Hz), 6.71 (1H, s), 2.52 (2H, q, J=7.5 Hz), 1.87-1.72 (1H, m), 1.16(3H, t, J=7.5 Hz), 0.80-0.65 (2H, m), 0.65-0.50 (2H, m). Appearance:amorphous.

EXAMPLE 270 6-Chloro-3-(2,6-dipropylphenoxy)-4-pyridazinol (Compound No.890)

Melting point (° C.): 191-193.

EXAMPLE 271 6-Chloro-3-(2,6-diisopropylphenoxy)-4-pyridazinol (CompoundNo. 894)

¹H-NMR (90 MHz, DMSO-d₆) δ ppm: 7.28 (3H, s), 6.80 (1H, s), 2.88 (2H,septet, J=7.0 Hz), 1.15 (12H, d, J=7.0 Hz). Melting point (° C.): >285.

EXAMPLE 272 6-Chloro-3-(2-cyclopropyl-6-isopropylphenoxy)-4-pyridazinol(Compound No. 896)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.22-7.12 (2H, m), 6.83 (1H, brs), 6.82(1H, dd, J=6.6, 2.2 Hz), 2.91 (1H, septet, J=7.0 Hz), 1.74-1.63 (1H, m),1.11 (6H, d, J=7.0 Hz), 0.75-0.71 (2H, m), 0.58-0.50 (2H, m). Meltingpoint (° C.): 242-245.

EXAMPLE 273 6-Chloro-3-(2-isopropyl-6-nitrophenoxy)-4-pyridazinol(Compound No. 911)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 8.00 (1H, d, J=7.7 Hz), 7.88 (1H, d,J=7.7 Hz), 7.54 (1H, t, J=7.7 Hz), 6.96 (1H, brs), 3.07 (1H, septet,J=7.0 Hz), 1.16 (6H, d, J=7.0 Hz). Melting point (° C.): 205-209.

EXAMPLE 274 3-(2-tert-Butyl-6-cyclopropylphenoxy)-6-chloro-4-pyridazinol(Compound No. 914)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.28 (1H, br.d, J=8.1 Hz), 7.10 (1H, dd,J=8.1 and 7.7 Hz), 6.90 (1H, d, J=7.7 Hz), 6.70 (1H, s), 1.80-1.55 (1H,m), 1.34 (9H, s), 0.85-0.60 (2H, m), 0.50-0.20 (2H, m) Melting point (°C.): 230-231.

EXAMPLE 275 6-Chloro-3-(2,6-dicyclopropylphenoxy)-4-pyridazinol(Compound No. 931)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.08 (1H, t, J=7.7 Hz), 6.81 (2H, d,J=7.7 Hz), 6.71 (1H, s), 1.95-1.75 (2H, m), 0.85-0.70 (4H, m), 0.70-0.50(4H, m). Melting point (° C.): 232-234.

EXAMPLE 276 6-Chloro-3-(2-cyclopropyl-6-methoxyphenoxy)-4-pyridazinol(Compound No. 964)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.13 (1H, t, J=8.1 Hz), 6.92 (1H, d,J=8.1 Hz), 6.81 (1H, brs), 6.54 (1H, d, J=8.1 Hz), 3.68 (3H, s),1.87-1.78 (1H, m), 0.87-0.78 (2H, m), 0.64-0.56 (2H, m). Melting point(° C.): 194-199.

EXAMPLE 277 6-Chloro-3-(2-cyclopropyl-6-ethoxyphenoxy)-4-pyridazinol(Compound No. 965)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.07 (1H, t, J=8.1 Hz), 6.84 (1H, dd,J=8.4, 1.5 Hz), 6.71 (1H, s), 6.54 (1H, dd, J=8.4, 1.5 Hz), 3.97 (2H, q,J=7.0 Hz), 2.04-1.91 (1H, m), 1.18 (3H, t, J=7.0 Hz), 0.89-0.79 (2H, m),0.66-0.60 (2H, m). Melting point (° C.): 174-179.

EXAMPLE 278 6-Chloro-3-{2,6-di[(1E)-1-propenyl]phenoxy}-4-pyridazinol(Compound No. 979)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.40 (2H, d, J=7.8 Hz), 7.15 (1H, t,J=7.8 Hz), 6.72 (1H, s), 6.34 (2H, d, J=16.4 Hz), 6.27 (2H, dd, J=16.4,4.9 Hz), 1.79 (6H, d, J=4.9 Hz) Melting point (° C.): 163-164.

EXAMPLE 279 6-Chloro-3-(2,6-diallylphenoxy)-4-pyridazinol (Compound No.982)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.20-7.15 (3H, m), 6.70 (1H, s),5.95-5.75 (2H, m), 5.02-4.87 (4H, m), 3.26 (4H, d, J=6.8 Hz). Meltingpoint (° C.): 131-135.

EXAMPLE 280 6-Chloro-3-(2,6-dimethoxyphenoxy)-4-pyridazinol (CompoundNo. 987)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.19 (1H t, J=8.3 Hz), 6.79-6.75 (3Hm), 3.71 (6H, s). Melting point (° C.): 199-201.

EXAMPLE 281 6-Chloro-3-(3,5-dimethylphenoxy)-4-pyridazinol (Compound No.998)

¹H-NMR (60 MHz, DMSO-d₆) δ ppm: 6.90-6.65 (4H, m), 2.27 (6H, s). Meltingpoint (° C.): 178-182.

EXAMPLE 282 6-Chloro-3-(3-isopropyl-5-methylphenoxy)-4-pyridazinol(Compound No. 1000)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.94 (1H, s), 6.84 (1H, s) 6.81 (1H, s),6.69 (1H, s), 2.87 (1H, septet, J=7.0 Hz), 2.32 (3H, s), 1.23 (6H, d,J=7.0 Hz). Melting point (° C.): 204-206.

EXAMPLE 283 6-Chloro-3-(3,5-diisopropylphenoxy)-4-pyridazinol (CompoundNo. 1007)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.98 (1H, s), 6.87 (1H, s) 6.86 (1H, s),6.68 (1H, s), 2.90 (2H, septet, J=7.0 Hz), 1.24 (12H, d, J=7.0 Hz).Melting point (° C.): 249-253.

EXAMPLE 284 3-[3,5-Bis(trifluoromethyl)phenoxy]-6-chloro-4-pyridazinol(Compound No. 1009)

¹H-NMR (200 MHz, DMF-d₇) δ ppm: 8.20-7.80 (3H, m), 6.94 (1H, s),5.50-4.50 (1H, brs). Melting point (° C.): 237-242.

EXAMPLE 285 3-(2-Bromo-3,5-dimethylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1013)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.11 (1H, s), 7.00 (1H, s), 6.86 (1H,brs), 2.37 (3H, s), 2.27 (3H, s). Melting point (° C.): 240-244.

EXAMPLE 286 6-Chloro-3-(2,3,5-trimethylphenoxy)-4-pyridazinol (CompoundNo. 1016)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 6.90 (1H, s), 6.75 (1H, s) 6.70 (1H, s),2.30 (6H, s), 2.02 (3H, s). Melting point (° C.): 223-224.

EXAMPLE 287 6-Chloro-3-(3,5-dimethyl-2-propylphenoxy)-4-pyridazinol(Compound No. 1020)

¹H-NMR (90 MHz, DMSO-d₆) δ ppm: 6.90 (1H, s), 6.81 (1H, s), 6.77 (1H,s), 2.29 (3H, s), 2.21 (3H, s), 2.53-2.19 (2H, m), 1.57-1.29 (2H, m),0.86 (3H, t, J=6.6 Hz). Melting point (° C.): 154.5.

EXAMPLE 288 6-Chloro-3-(2-cyclopropyl-3,5-dimethylphenoxy)-4-pyridazinol(Compound No. 1023)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.89 (1H, s), 6.73 (1H, s) 6.69 (1H, s),2.39 (3H, s), 2.26 (3H, s), 1.45-1.28 (1H, m), 0.78-0.67 (2H, m),0.65-0.51 (2H, m). Melting point (° C.): 200-203.

EXAMPLE 2896-Chloro-3-[3,5-dimethyl-2-(methylsulfanyl)phenoxy]-4-pyridazinol(Compound No. 1027)

Melting point (° C.): 213-214.

EXAMPLE 290 3-(2-Bromo-3,6-dimethylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1040)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.16 (1H, d, J=7.9 Hz), 7.10 (1H, d,J=7.9 Hz), 6.72 (1H, s), 2.38 (3H, s), 2.16 (3H, s). Melting point (°C.): 255-257.

EXAMPLE 291 3-(6-Bromo-3-fluoro-2-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1050)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.51 (1H, dd, J=8.8, 5.9 Hz), 7.00 (1H,t, J=8.8 Hz), 6.96 (1H, s), 2.13 (3H, d, J=2.2 Hz). Appearance:amorphous.

EXAMPLE 292 3-(6-Bromo-3-chloro-2-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1053)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.47 (1H, d, J=8.1 Hz), 7.23 (1H, d,J=8.1 Hz), 6.64 (1H, s), 2.24 (3H, s). Melting point (° C.): 254-260.

EXAMPLE 2936-Chloro-3-(3-chloro-6-cyclopropyl-2-methylphenoxy)-4-pyridazinol(Compound No. 1055)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.18 (1H, d, J=8.4 Hz), 6.81 (1H, d,J=8.4 Hz), 6.64 (1H, s), 2.17 (3H, s), 1.89-1.76 (1H, m), 0.80-0.71 (2H,m), 0.68-0.51 (2H, m). Melting point (° C.): 233.

EXAMPLE 294 3-(6-Bromo-2,3-dimethylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1058)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.34 (1H, d, J=8.1 Hz), 6.99 (1H, d,J=8.1 Hz), 6.71 (1H, s), 2.28 (3H, s), 2.12 (3H, s). Melting point (°C.): 263-268.

EXAMPLE 295 6-Chloro-3-(2,3,6-trimethylphenoxy)-4-pyridazinol (CompoundNo. 1060)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.0 (2H, s), 6.73 (1H, s), 2.27 (3H, s),2.07 (3H, s), 2.03 (3H, s). Melting point (° C.): 228.

EXAMPLE 296 6-Chloro-3-(6-cyclopropyl-2,3-dimethylphenoxy)-4-pyridazinol(Compound No. 1061)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.96 (1H, d, J=8.1 Hz), 6.72 (1H, d,J=8.1 Hz), 6.69 (1H, s), 2.24 (3H, s), 2.04 (3H, s), 1.85-1.70 (1H, m),0.75-0.46 (4H, m). Melting point (° C.): 229-234.

EXAMPLE 2972-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-3,4-dimethylbenzaldehyde0-methyloxime (Compound No. 1063)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.98 (1H, s), 7.50 (1H, d, J=8.1 Hz),7.11 (1H, d, J=8.1 Hz), 6.69 (1H, s), 3.81 (3H, s), 2.32 (3H, s), 2.06(3H, s). Appearance: amorphous.

EXAMPLE 298 6-Chloro-3-(6-methoxy-2,3-dimethylphenoxy)-4-pyridazinol(Compound No. 1064)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.00 (1H, d, J=8.4 Hz), 6.78 (1H, d,J=8.4 Hz), 6.66 (1H, s), 3.69 (3H, s), 2.23 (3H, s), 2.08 (3H, s).Appearance: amorphous.

EXAMPLE 299 3-(6-Bromo-3-methoxy-2-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1066)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.42 (1H, d, J=9.2 Hz), 6.82 (1H, d,J=9.2 Hz), 6.69 (1H, s), 3.86 (3H, s), 2.05 (3H, s). Melting point (°C.): 246-253.

EXAMPLE 3006-Chloro-3-(6-cyclopropyl-3-methoxy-2-methylphenoxy)-4-pyridazinol(Compound No. 1069)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.83 (1H, d, J=8.8 Hz), 6.75 (1H, d,J=8.8 Hz), 6.66 (1H, s), 3.81 (3H, s), 1.99 (3H, s), 1.78-1.70 (1H, m),0.69-0.63 (2H, m), 0.52-0.47 (2H, m). Melting point (° C.): 250-253.

EXAMPLE 301 6-Chloro-3-(2-cyclopropyl-3,6-dimethylphenoxy)-4-pyridazinol(Compound No. 1073)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.20 (1H, d, J=7.6 Hz), 6.95 (1H, d,J=7.6 Hz), 6.68 (1H, s), 2.39 (3H, s), 2.10 (3H, s), 1.50-1.25 (1H, m),0.90-0.70 (2H, m), 0.70-0.50 (2H, m). Melting point (° C.): 171-175.

EXAMPLE 302 3-(2-Allyl-6-ethyl-3-methoxyphenoxy)-6-chloro-4-pyridazinol(Compound No. 1080)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.11 (1H, d, J=8.4 Hz), 6.85 (1H, s),6.83 (1H, d, J=8.4 Hz), 6.10-5.30 (1H, m), 5.00-4.60 (2H, m), 3.83 (3H,s), 3.30-3.10 (2H, m), 2.40 (2H, q, J=7.6 Hz), 1.10 (3H, t, J=7.6 Hz).Melting point (° C.): 183-186.

EXAMPLE 3036-Chloro-3-{3,6-dimethyl-2-[(methylsulfanyl)methyl]-phenoxy}-4-pyridazinol(Compound No. 1083)

¹H-NMR (90 MHz, CD₃OD) δ ppm: 7.21-6.90 (2H, m), 6.71 (1H, s), 3.68 (2H,s), 2.38 (3H, s), 2.09 (3H, s), 2.00 (3H, s). Appearance: amorphous.

EXAMPLE 3043-[(5-Bromo-2,3-dihydro-1H-inden-4-yl)oxy]-6-chloro-4-pyridazinol(Compound No. 1086)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.39 (1H, d, J=8.1 Hz), 7.05 (1H, d,J=8.1 Hz), 6.71 (1H, s), 2.94 (2H, t, J=7.3 Hz), 2.79 (2H, t, J=7.3 Hz),2.10-2.00 (2H, m). Appearance: amorphous.

EXAMPLE 3056-Chloro-3-[(5-methyl-2,3-dihydro-1H-inden-4-yl)oxy]-4-pyridazinol(Compound No. 1088)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.11-7.01 (2H, m), 6.83 (1H, brs), 2.88(3H, t, J=7.3 Hz), 2.59 (3H, t, J=7.3 Hz), 2.06 (3H, s), 2.06-1.91 (2H,m). Melting point (° C.): 222-225.

EXAMPLE 3066-Chloro-3-[(5-ethyl-2,3-dihydro-1H-inden-4-yl)oxy]-4-pyridazinol(Compound No. 1089)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.06 (2H, s), 6.71 (1H, S) 2.91 (2H, t,J=7.3 Hz), 2.67 (2H, t, J=7.3 Hz), 2.51 (2H, q, J=7.7 Hz), 2.04 (2H,quintet, J=7.3 Hz), 1.13 (3H, t, J=7.7 Hz). Melting point (° C.):193-196.

EXAMPLE 3076-Chloro-3-[(5-cyclopropyl-2,3-dihydro-1H-inden-4-yl)oxy]-4-pyridazinol(Compound No. 1091)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.02 (1H, d, J=7.7 Hz), 6.79 (1H, d,J=7.7 Hz), 6.71 (1H, s), 2.90 (2H, t, J=7.3 Hz), 2.72 (2H, t, J=7.3 Hz),2.18-1.98 (2H, m), 1.92-1.75 (1H, m), 0.82-0.70 (2H, m), 0.60-0.47 (2H,m). Melting point (° C.): 218-220.

EXAMPLE 3086-Chloro-3-[(6-methyl-2,3-dihydro-1-benzofuran-7-yl)oxy]-4-pyridazinol(Compound No. 1096)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.99 (1H, d, J=7.7 Hz), 6.72 (1H, d,J=7.7 Hz), 6.70 (1H, s), 4.53 (2H, t, J=8.8 Hz), 3.20 (2H, br.t, J=8.8Hz), 2.15 (3H, s). Melting point (° C.): 217-219.

EXAMPLE 309 3-[(6-Bromo-1-benzofuran-7-yl)oxy]-6-chloro-4-pyridazinol(Compound No. 1099)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.75 (1H, d, J=2.2 Hz), 7.48 (1H, d,J=8.4 Hz), 7.47 (1H, d, J=8.4 Hz), 6.92 (1H, d, J=2.2 Hz), 6.78 (1H, s)Appearance: amorphous.

EXAMPLE 310 6-Chloro-3-[(6-methyl-1-benzofuran-7-yl)oxy]-4-pyridazinol(Compound No. 1100)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.65 (1H, d, J=2.2 Hz), 7.40 (1H, d,J=8.1 Hz), 7.14 (1H, d, J=8.1 Hz), 6.82 (1H, d, J=2.2 Hz), 6.75 (1H, s),2.31 (3H, s). Appearance: oily product.

EXAMPLE 3116-Chloro-3-[(6-cyclopropyl-1-benzofuran-7-yl)oxy]-4-pyridazol (CompoundNo. 1102)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.65 (1H, d, J=2.2 Hz), 7.40 (1H, d,J=8.1 Hz), 6.87 (1H, d, J=8.1 Hz), 6.81 (1H, d, J=2.2 Hz), 6.75 (1H, s),2.10-1.98 (1H, m), 0.98-0.80 (2H, m), 0.80-0.64 (2H, m) Melting point (°C.): 175-180.

EXAMPLE 312 6-Chloro-3-[(5-methyl-1-benzofuran-4-yl)oxy]-4-pyridazinol(Compound No. 1109)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.65 (1H, d, J=2.2 Hz), 7.32 (1H, d,J=8.4 Hz), 7.18 (1H, d, J=8.4 Hz), 6.73 (1H, s), 6.60 (1H, d, J=2.2 Hz),2.23 (3H, s). Melting point (° C.): 222-225.

EXAMPLE 313 6-Chloro-3-(2,4-dicyclopropyl-6-fluorophenoxy)-4-pyridazinol(Compound No. 1115)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.71-6.65 (2H, m), 6.54 (1H, s),2.02-1.81 (2H, m), 1.01-0.72 (4H, m), 0.68-0.60 (4H, m). Appearance:amorphous.

EXAMPLE 314 6-Chloro-3-(2,4-dibromo-3,6-dimethylphenoxy)-4-pyridazinol(Compound No. 1118)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.54 (1H, s), 6.71 (1H, s), 2.56 (3H, s),2.16 (3H, s). Melting point (° C.): 241-248.

EXAMPLE 315 3-(2-Bromo-4,6-dimethylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1119)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.31 (1H, brs), 7.10 (1H, brs), 6.74 (1H,s), 2.31 (3H, s), 2.17 (3H, s). Melting point (° C.): 254-256.

EXAMPLE 316 6-Chloro-3-(2-ethyl-4,6-diiodophenoxy)-4-pyridazinol(Compound No. 1120)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.03 (1H, d, J=2.2 Hz), 7.66 (1H, d,J=2.2 Hz), 6.74 (1H, s), 2.52 (2H, q, J=7.7 Hz), 1.17 (3H, t, J=7.7 Hz).Melting point (° C.): 142-144.

EXAMPLE 317 6-Chloro-3-(2,4,6-trimethylphenoxy)-4-pyridazinol (CompoundNo. 1122)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.90 (2H, s), 6.71 (1H, s), 2.27 (3H, s),2.07 (6H, s). Melting point (° C.): 235-239.

EXAMPLE 318 6-Chloro-3-(2-cyclopropyl-4,6-dimethylphenoxy)-4-pyridazinol(Compound No. 1123)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.88 (1H, brs), 6.69 (1H, s), 6.63 (1H,brs), 2.26 (3H, s), 2.09 (3H, s), 1.85-1.70 (1H, m), 0.80-0.65 (2H, m),0.65-0.50 (2H, m). Melting point (° C.): 215-217.

EXAMPLE 319 3-(2-Bromo-3,5,6-trimethylphenoxy)-6-chloro-4-pyridazinol(Compound No. 1124)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.13 (1H, s), 6.88 (1H, brs), 2.32 (3H,s), 2.23 (3H, s), 2.01 (3H, s). Melting point (° C.): 280-290.

EXAMPLE 320 6-Chloro-3-(2,3,5,6-tetramethylphenoxy)-4-pyridazinol(Compound No. 1125)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.88 (1H, s), 6.69 (1H, s), 2.22 (6H, s),1.98 (6H, s). Melting point (° C.): 278-283.

EXAMPLE 3216-Chloro-3-[(5,6-dimethyl-2,3-dihydro-1H-inden-4-yl)oxy]-4-pyridazinol(Compound No. 1129)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.72 (1H, s), 6.68 (1H, s), 2.88 (2H, t,J=7.4 Hz), 2.70 (2H, t, J=7.4 Hz), 2.24 (3H, s), 2.17 (3H, s), 2.05 (2H,quintet, J=7.4 Hz). Melting point (° C.): 210-213.

EXAMPLE 3226-Chloro-3-(1,2,3,5,6,7-hexahydro-s-indacen-4-yloxy)-4-pyridazinol(Compound No. 1133)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.95 (1H, s), 6.65 (1H, s), 2.88 (4H, t,J=7.3 Hz), 2.68 (4H, t, J=7.3 Hz), 2.20-1.90 (4H, m). Appearance:amorphous.

EXAMPLE 323 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl acetate(Compound No. 1140)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.40 (1H, s), 7.26-6.98 (4H, m), 2.40(3H, s), 1.93-1.76 (1H, m), 0.85-0.59 (4H, m). Appearance: amorphous.

EXAMPLE 324 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylacetate (Compound No. 1151)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.39 (1H, s), 7.15-7.00 (2H, m),6.90-6.75 (1H, m), 2.42 (3H, s), 2.12 (3H, s), 1.90-1.67 (1H, m),0.85-0.50 (4H, m). Melting point (° C.): 98-101.

EXAMPLE 325 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylpivalate (Compound No. 1207)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.38 (1H, s), 7.15-7.05 (2H, m),6.90-6.84 (1H, m), 2.13 (3H, s), 1.81-1.65 (1H, m), 1.41 (9H, s),0.90-0.50 (4H, m). Melting point (° C.): 84-87.

EXAMPLE 326 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldecanoate (Compound No. 1251)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.38 (1H, s), 7.15-7.05 (2H, m),6.93-6.80 (1H, m), 2.67 (2H, t, J=7.3 Hz), 2.12 (3H, s), 1.85-1.65 (3H,m), 1.55-1.10 (12H, m), 0.95-0.80 (3H, m), 0.80-0.65 (2H, m), 0.65-0.52(2H, m). Appearance: oily product.

EXAMPLE 327 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinylcyclopropanecarboxylate (Compound No. 1266)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.43 (1H, s), 7.22-6.98 (4H, m),2.00-1.75 (2H, m), 1.30-1.08 (4H, m), 0.86-0.51 (4H, m). Melting point(° C.): 122-125.

EXAMPLE 328 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl benzoate(Compound No. 1387)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.23-8.18 (2H, m), 7.75-7.50 (3H, m),7.60 (1H, s) 7.30-7.08 (4H, m), 2.18 (3H, s). Appearance: oily product.

EXAMPLE 329 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl benzoate(Compound No. 1391)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.20 (2H, d, J=7.3 Hz), 7.74-7.50 (4H,m), 7.26-7.01 (3H, m), 6.98-6.97 (1H, m), 1.91-1.80 (1H, m), 0.83-0.57(4H, m). Appearance: amorphous.

EXAMPLE 330 6-Chloro-3-[4-(trimethylsilyl)phenoxy]-4-pyridazinylbenzoate (Compound No. 1396)

Melting point (° C.): 100-102.

EXAMPLE 331 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbenzoate (Compound No. 1417)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.24-8.20 (2H, m), 7.75-7.68 (2H, m),7.67-7.52 (3H, m), 7.09-7.07 (2H, m), 6.87-6.82 (1H, m), 2.16 (3H, s),1.82-1.71 (1H, m), 0.75-0.71 (2H, m), 0.62-0.53 (2H, m) Appearance:amorphous.

EXAMPLE 332 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl 2-methylbenzoate(Compound No. 1446)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.35-8.08 (2H, m), 7.59 (1H, s), 7.68-7.00(6H, m), 2.70 (3H, s), 2.21 (3H, s). Melting point (° C.): 91-93.

EXAMPLE 333 6-Chloro-3-(2-isopropylphenoxy)-4-pyridazinyl2-methylbenzoate (Compound No. 1448)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.15-8.00 (2H, m), 7.58 (1H, s), 7.75-6.90(6H, m), 3.40-2.85 (1H, m), 2.69 (3H, s), 1.15 (6H, d, J=7.0 Hz).

Refractive index: n_(D) ²² 1.5709.

EXAMPLE 334 3-(2-s-Butylphenoxy)-6-chloro-4-pyridazinyl 2-methylbenzoate(Compound No. 1450)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.28-8.05 (1H, m), 7.60-7.05 (7H, m), 7.52(1H, s), 3.05-2.60 (1H, m), 2.65 (3H, s), 1.70-1.00 (2H, m), 1.10 (3H,d, J=7.0 Hz), 0.90-0.50 (3H, m). Appearance: paste state.

EXAMPLE 335 6-Chloro-3-(2-cyclohexylphenoxy)-4-pyridazinyl2-methylbenzoate (Compound No. 1455)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.30-7.00 (8H, m), 7.54 (1H, s), 2.68 (1H,brs), 2.67 (3H, s), 2.00-1.00 (10H, m). Melting point (° C.): 89-91.

EXAMPLE 336 3-([1,1′-Biphenyl]-2-yloxy)-6-chloro-4-pyridazinyl2-methylbenzoate (Compound No. 1456)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.20-7.90 (1H, m), 7.60-7.10 (13H, m),2.58 (3H, s).

Refractive index: n_(D) ²⁸ 1.6055.

EXAMPLE 337 3-(3-tert-Butylphenoxy)-6-chloro-4-pyridazinyl2-methylbenzoate (Compound No. 1457)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.28-8.02 (1H, m), 7.55 (1H, s), 7.65-6.85(7H, m), 2.64 (3H, s), 1.28 (9H, s). Melting point (° C.): 63-64.

EXAMPLE 338 6-Chloro-3-(3-methoxyphenoxy)-4-pyridazinyl 2-methylbenzoate(Compound No. 1458)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.30-8.00 (1H, m), 7.70-7.10 (4H, m), 7.55(1H, s), 6.90-6.60 (3H, m), 3.74 (3H, s), 2.64 (3H, s). Melting point (°C.): 66-67.

EXAMPLE 339 6-Chloro-3-(2-isopropyl-5-methylphenoxy)-4-pyridazinyl2-methylbenzoate (Compound No. 1459)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.30-8.00 (1H, m), 7.54 (1H, s), 7.50-6.80(6H, m), 3.30-2.75 (1H, m), 2.65 (3H, s), 2.28 (3H, s), 1.15 (6H, d,J=7.00 Hz). Melting point (° C.): 95-97.

EXAMPLE 340 6-Chloro-3-(1-naphthyloxy)-4-pyridazinyl 2-methylbenzoate(Compound No. 1461)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.20-7.00 (12H, m), 2.65 (3H, s) Meltingpoint (° C.): 133-134.

EXAMPLE 341 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl 2-methoxybenzoate(Compound No. 1509)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.11-7.89 (2H, m), 7.70-6.80 (6H, m), 7.50(1H, s), 3.84 (3H, s), 2.10 (3H, s). Melting point (° C.): 114-116.

EXAMPLE 342 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl 4-methylbenzoate(Compound No. 1553)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.07 (2H, d, J=8.0 Hz), 7.58 (1H, s),7.40-7.03 (4H, m), 7.36 (2H, d, J=8.0 Hz), 2.51 (3H, s), 2.23 (3H, s).Melting point (° C.): 105-108.

EXAMPLE 343 6-Chloro-3-(2-isopropylphenoxy)-4-pyridazinyl4-methylbenzoate (Compound No. 1554)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.28-7.82 (2H, m), 7.61 (1H, s), 7.51-6.90(6H, m), 3.30-2.80 (1H, m), 2.46 (3H, s), 1.19 (6H, d, J=7.0 Hz).

Refractive index: n_(D) ²² 1.5731.

EXAMPLE 344 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl2,4-dichlorobenzoate (Compound No. 1603)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.04 (1H, d, J=8.4 Hz), 7.58 (1H, s),7.58-6.92 (6H, m), 2.20 (3H, s). Melting point (° C.): 81-82.5.

EXAMPLE 345 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl methylcarbonate (Compound No. 1658)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.51 (1H, s), 7.23-6.98 (4H, m), 3.99(3H, s), 1.91-1.82 (1H, m), 0.84-0.61 (4H, m). Appearance: amorphous.

EXAMPLE 346 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl ethyl carbonate(Compound No. 1706)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.51 (1H, s), 7.38-7.00 (4H, m), 4.40 (2H,q, J=7.0 Hz), 2.20 (3H, s), 1.40 (3H, t, J=7.0 Hz). Melting point (°C.): 73-74.

EXAMPLE 347 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl ethylcarbonate (Compound No. 1710)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.51 (1H s), 7.26-6.98 (4H, m), 4.40 (2H,q, J=7.0 Hz), 1.90-1.80 (1H, m), 1.41 (3H, t, J=7.0 Hz), 0.84-0.60 (4H,m). Appearance: amorphous.

EXAMPLE 348 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl isobutylcarbonate (Compound No. 1757)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.45 (1H, s), 7.30-7.00 (4H, m), 4.08 (2H,d, J=5.8 Hz), 2.16 (3H, s), 2.20-1.70 (1H, m), 0.96 (6H, d, J=5.8 Hz).Melting point (° C.): 46-47.

EXAMPLE 349 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl2,2,2-trichloroethyl carbonate (Compound No. 1789)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.52 (1H, s), 7.28-7.03 (4H, m), 4.94(2H, s), 2.18 (3H, s). Appearance: amorphous.

EXAMPLE 350 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylphenyl carbonate (Compound No. 1840)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.50-7.20 (5H, m),7.20-7.05 (2H, m), 6.92-6.82 (1H, m), 2.16 (3H, s), 1.88-1.72 (1H, m),0.80-0.55 (4H, m). Appearance: oily product.

EXAMPLE 351 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl dimethylcarbamate(Compound No. 1877)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.55 (1H, s), 7.40-6.92 (4H, m), 3.10 (3H,s), 3.01 (3H, s), 2.19 (3H, s). Melting point (° C.): 107-109.

EXAMPLE 352 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyldimethylcarbamate (Compound No. 1879)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.22-6.98 (4H, m), 3.13(3H, s), 3.04 (3H, s), 1.97-1.80 (1H, m), 0.85-0.63 (4H, m). Meltingpoint (° C.): 137-138.

EXAMPLE 353 6-Chloro-3-[3-(trifluoromethyl)phenoxy]-4-pyridazinyldimethylcarbamate (Compound No. 1881)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.60 (1H, s), 7.65-7.22 (4H, m), 3.11 (3Hs), 3.05 (3H s). Melting point (° C.): 92-93.

EXAMPLE 354 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl diethylcarbamate(Compound No. 1898)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.55 (1H, s), 7.40-6.92 (4H, m), 3.41 (4H,q, J=6.2 Hz), 2.20 (3H, s), 1.27 (6H, t, J=6.2 Hz). Melting point (°C.): 74-75.5.

EXAMPLE 355 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl1-pyrrolidinecarboxylate (Compound No. 1924)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.42-7.02 (4H, m), 3.67-3.37(4H, m), 2.19 (3H, s), 2.07-1.72 (4H, m). Melting point (° C.): 126-127.

EXAMPLE 356 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl methanesulfonate(Compound NO. 1981)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.55 (1H, s), 7.33-7.06 (4H, m), 3.43(3H, s), 2.20 (3H, s) Appearance: oily product.

EXAMPLE 357 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinylmethanesulfonate (Compound No. 1985)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.55 (1H, s), 7.26-7.23 (2H, m),7.21-7.02 (2H, m), 3.44 (3H, s), 1.89-1.80 (1H, m), 0.86-0.61 (4H, m)Melting point (° C.): 162-172.

EXAMPLE 358 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethanesulfonate (Compound No. 2010)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56 (1H, s), 7.18-7.09 (2H, m),6.91-6.86 (1H, m), 3.47 (3H, s), 2.16 (3H, s), 1.82-1.68 (1H, m),0.75-0.69 (2H, m), 0.67-0.55 (2H, m). Appearance: amorphous.

EXAMPLE 359 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl1-propanesulfonate (Compound No. 2038)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.34-7.05 (4H, m), 3.48(2H, t, J=7.7 Hz), 2.20 (3H, s), 2.10 (2H, sixtet, J=7.7 Hz), 1.14 (3H,t, J=7.7 Hz). Melting point (° C.): 72-73.

EXAMPLE 360 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl1-propanesulfonate (Compound No. 2040)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.28-7.15 (2H, m),7.12-6.99 (2H, m), 3.52-3.45 (2H, m), 2.17-1.98 (2H, m), 1.92-1.78 (1H,m), 1.11 (3H, t, J=7.3 Hz), 0.85-0.73 (2H, m), 0.69-0.60 (2H, m).Appearance: paste state.

EXAMPLE 361 6-Chloro-3-(2,3-dihydro-1H-inden-4-yloxy)-4-pyridazinyl1-propanesulfonate (Compound No. 2042)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56 (1H, s), 7.26-7.14 (2H, m), 6.94(1H, dd, J=7.0, 1.8 Hz), 3.50-3.42 (2H, m), 2.98 (2H, t, J=7.3 Hz), 2.74(2H, t, J=7.3 Hz), 2.17-1.98 (4H, m), 1.12 (3H, t, J=7.3 Hz).Appearance: paste state.

EXAMPLE 3626-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-5-iodo-4-pyridazinol(Compound No. 3849)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.08-7.05 (2H, m), 6.84-6.80 (1H, m),2.14 (3H, s), 1.86-1.75 (1H, m), 0.81-0.65 (2H, m), 0.60-0.52 (2H, m)Appearance: amorphous.

EXAMPLE 363 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyltrifluoromethanesulfonate (Compound No. 2106)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.52 (1H, s), 7.19-7.09 (2H, m),6.96-6.89 (1H, m), 2.15 (3H, s), 1.81-1.67 (1H, m), 0.73-0.58 (4H, m)Melting point (° C.): 64-67.

EXAMPLE 364 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl benzenesulfonate(Compound No. 2147)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.10-7.83 (2H, m), 7.80-7.40 (3H, m), 7.59(1H, s), 7.30-7.00 (3H, m), 6.90-6.60 (1H, m). Melting point (° C.):91.5-92.

EXAMPLE 365 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinylbenzenesulfonate (Compound No. 2151)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.02-7.98 (2H, m), 7.78-7.70 (1H, m),7.62-7.54 (2H, m), 7.58 (1H, s), 7.26-7.09 (2H, m), 6.98-6.93 (1H, m),6.78-6.69 (1H, m), 1.68-1.54 (1H, m), 0.74-0.52 (4H, m). Appearance:oily product.

EXAMPLE 366 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbenzenesulfonate (Compound No. 2176)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.07-8.01 (2H, m), 7.80-7.71 (1H, m),7.65-7.56 (2H, m), 7.60 (1H, s), 7.11-6.99 (2H, m), 6.80 (1H, dd, J=4.4,2.4 Hz), 1.93 (3H, s), 1.61-1.45 (1H, m), 0.65-0.45 (4H, m). Meltingpoint (° C.): 105-106.

EXAMPLE 367 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl4-chlorobenzenesulfonate (Compound No. 2198)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.94 (2H, d, J=8.4 Hz), 7.60 (1H, s), 7.59(2H, d, J=8.4 Hz), 7.23-7.09 (3H, m), 6.90-6.60 (1H, m), 2.93 (3H, s).Melting point (° C.): 93-94.

EXAMPLE 368 3-(2-Isopropylphenoxy)-4-pyridazinyl4-chlorobenzenesulfonate (Compound No. 2199)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.91 (2H, d, J=8.4 Hz), 7.62 (1H, s), 7.55(2H, d, J=8.4 Hz), 7.50-7.00 (3H, m), 6.80-6.60 (1H, m), 3.20-2.50 (1H,m), 1.14 (6H, d, J=7.0 Hz).

Refractive index: n_(D) ²² 1.5315.

EXAMPLE 369 3-(2-tert-Butylphenoxy)-6-chloro-4-pyridazinyl4-chlorobenzenesulfonate (Compound No. 2200)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.05-7.05 (8H, m), 6.70-6.40 (1H, m),1.26. (9H, s) Melting point (° C.): 83.5-84.5.

EXAMPLE 370 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2220)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.83 (2H, d, J=8.4 Hz), 7.47 (2H, d, J=8.4Hz), 7.32-6.95 (4H, m), 6.85-6.55 (1H, m), 2.43 (3H, s), 1.98 (3H, s).Melting point (° C.): 102-104.

EXAMPLE 371 6-Chloro-3-(2-ethylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2221)

Refractive index: n_(D) ²⁸ 1.5847.

EXAMPLE 372 6-Chloro-3-(2-isopropylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2222)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.00-6.50 (8H, m), 7.55 (1H, s), 2.85 (1H,septet, J=7.0 Hz), 2.42 (3H, s), 1.11 (6H, d, J=7.0 Hz). Melting point(° C.): 99-100.

EXAMPLE 373 3-(2-s-Butylphenoxy)-6-chloro-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2223)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.98-6.50 (8H, m), 7.52 (1H, s), 2.99-2.31(1H, m), 2.41 (3H, s), 1.82-0.95 (2H, m), 1.08 (3H, d, J=7.0 Hz),0.90-0.35 (3H, m). Melting point (° C.): 65-66.

EXAMPLE 374 3-(2-tert-Butylphenoxy)-6-chloro-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2224)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.98-7.00 (7H, m), 7.61 (1H s), 6.78-6.45(1H, m), 2.40 (3H, s), 1.29 (9H, s). Melting point (° C.): 98-99.

EXAMPLE 375 5,6-Dichloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol(Compound No. 3837)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.08-7.06 (2H, m), 6.85-6.80 (1H, m),2,14 (3H, s), 1.87-1.78 (1H, m), 0.81-0.72 (2H, m), 0.64-0.52 (2H, m)Appearance: amorphous.

EXAMPLE 376 6-Chloro-3-(2-cyclohexylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2230)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.00-6.50 (8H, m), 7.50 (1H, s), 2.50 (1H,brs), 2.40 (3H, s), 2.00-0.90 (1OH, m). Melting point (° C.): 120-121.

EXAMPLE 377 3-([1,1′-Biphenyl]-2-yloxy)-6-chloro-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2231)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.80-6.60 (14H, m), 2.42 (3H, s). Meltingpoint (° C.): 106-108.

EXAMPLE 378 6-Chloro-3-(2-methoxyphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2232)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.00-6.70 (8H, m), 7.56 (1H, s), 3.62 (3H,s), 2.44 (3H, s). Melting point (° C.): 153-157.

EXAMPLE 379 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylpropionate (Compound No. 1160)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.39 (1H, s), 7.14-7.05 (2H, m),6.89-6.82 (1H, m), 2.72 (2H, q, J=7.6 Hz), 2.12 (3H, s), 1.82-1.68 (1H,m), 1.31 (3H, t, J=7.6 Hz), 0.77-0.53 (4H, m). Melting point (° C.):75-77.

EXAMPLE 380 6-Chloro-3-(3-chlorophenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2234)

Refractive index: n_(D) ²⁸ 1.5970.

EXAMPLE 381 3-(3-tert-Butylphenoxy)-6-chloro-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2235)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.73 (2H, d, J=8.2 Hz), 7.49 (1H, s), 7.23(2H, d, J=8.2 Hz), 7.14 (1H, d, J=4.0 Hz), 6.90-6.45 (3H, m), 2.38 (3H,s), 1.26 (9H, s). Melting point (° C.): 56-57.

EXAMPLE 382 6-Chloro-3-[3-(trifluoromethyl)phenoxy]-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2236)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.95-6.93 (9H, m), 2.40 (3H, s).

Refractive index: n_(D) ^(25.5) 1.5556.

EXAMPLE 383 6-Chloro-3-(3-cyanophenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2237)

¹H-NMR (90 MHz, CDCl₃) δ ppm: 7.85 (2H, d, J=8.0 Hz), 7.70-7.00 (7H, m),2.49 (3H, s). Appearance: paste state.

EXAMPLE 384 6-Chloro-3-(3-methoxyphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2238)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.90-6.30 (8H, m), 7.47 (1H, s), 3.71 (3H,s), 2.40 (3H, s). Melting point (° C.): 89-90.

EXAMPLE 385 6-Chloro-3-(1-naphthyloxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2240)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.90-6.80 (12H, m), 2.38 (3H, s). Meltingpoint (° C.): 92-94.

EXAMPLE 386 3-(2-Bromo-4-tert-butylphenoxy)-6-chloro-6-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2245)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.89 (2H, d, J=8.4 Hz), 7.63 (1H, s),7.62-7.18 (3H, m), 6.84 (2H, d, J=8.4 Hz), 2.43 (3H, s), 1.29 (9H, s)Melting point (° C.): 110-112.

EXAMPLE 387 6-Chloro-3-(4-chloro-2-methylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2246)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.95-7.75 (2H, m), 7.60-7.00 (5H, m),6.80-6.60 (1H, m), 2.46 (3H, s), 2.00 (3H, s). Melting point (° C.):115-116.

EXAMPLE 388 6-Chloro-3-(2,4-dimethylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2247)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.94-7.78 (2H, m), 7.54 (1H, s), 7.41-7.23(2H, m), 7.02-6.53 (3H, m), 2.46 (3H, s), 2.30 (3H, s), 1.96 (3H, s).Melting point (° C.): 80-81.

EXAMPLE 389 3-(4-Bromo-2-isopropylphenoxy)-6-chloro-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2248)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.80 (2H, d, J=8.4 Hz), 7.51 (1H, s),7.45-7.10 (3H, m), 6.56 (2H, d, J=8.4 Hz), 2.85 (1H, septet, J=6.8 Hz),2.43 (3H, s), 1.10 (6H, d, J=6.8 Hz). Melting point (° C.): 119-122.

EXAMPLE 390 6-Chloro-3-(2-isopropyl-5-methylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2249)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.00-6.80 (6H, m), 7.56 (1H, s), 6.46 (1H,brs), 2.95-2.50 (1H, m), 2.44 (3H, s), 2.25 (3H, s), 1.09. (6H, d, J=7.0Hz). Melting point (° C.): 90-92.

EXAMPLE 391 6-Chloro-3-(2,6-dimethylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2263) Melting point (° C.):89-90. EXAMPLE 3926-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate (Compound No. 2265)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.90 (2H, d, J=8.1 Hz), 7.60 (1H, s),7.38 (2H, d, J=8.1 Hz), 7.11-7.01 (2H, m), 6.80 (1H, dd, J=6.6, 2.6 Hz),2.47 (3H, s), 1.93 (3H, s), 1.59-1.46 (1H, m), 0.64-0.45 (4H, m).Melting point (° C.): 85-87.

EXAMPLE 393 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl4-nitrobenzenesulfonate (Compound No. 2287)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 8.41 (2H, d, J=8.4 Hz), 8.33 (2H, d, J=8.4Hz), 7.61 (1H, s), 7.30-7.02 (3H, m), 6.95-6.63 (1H, m), 2.03 (3H, s).Melting point (° C.): 166-169.

EXAMPLE 394 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyl4-nitrobenzenesulfonate (Compound No. 2289)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.39 (2H, d, J=8.8 Hz), 8.23 (2H, d,J=8.8 Hz), 7.59 (1H, s), 7.20-7.09 (2H, m), 6.97-6.92 (1H, m), 6.77-6.73(1H, m), 1.67-1.59 (1H, m), 0.78-0.54 (4H, m). Melting point (° C.):158.

EXAMPLE 395 6-Chloro-3-(2-cyclopropylphenoxy)-4-pyridazinyldimethylsulfamate (Compound No. 2351)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.60 (1H, s), 7.26-7.01 (4H, m), 3.09(6H, s), 1.95-1.78 (1H, m), 0.85-0.63 (4H, m). Appearance: oily product.

EXAMPLE 396 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methylpropanoate (Compound No. 1172)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.38 (1H, s), 7.14-7.05 (2H, m),6.90-6.83 (1H, m), 2.93 (1H, septet, J=7.0 Hz), 2.13 (3H, s), 1.80-1.66(1H, m), 1.36 (6H, d, J=7.0 Hz), 0.78-0.56 (4H, m). Melting point (°C.): 38-39.

EXAMPLE 397 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylpentanoate (Compound No. 1178)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.38 (1H, s), 7.13-7.00 (2H, m),6.90-6.77 (1H, m), 2.68 (2H, t, J=7.3 Hz), 2.12 (3H, s), 1.88-1.65 (3H,m), 1.60-1.35 (2H, m), 0.95 (3H, t, J=7.3 Hz), 0.80-0.50 (4H, m).Appearance: caramel-like.

EXAMPLE 398 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-methylbutanoate (Compound No. 1184)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.37 (1H, s), 7.14-7.07 (2H, m),6.89-6.82 (1H, m), 2.55 (2H, d, J=7.0 Hz), 2.27 (1H, br.septet, J=6.8Hz), 2.12 (3H, s), 1.80-1.67 (1H, m), 1.07 (6H, d, J=6.6 Hz), 0.77-0.55(4H, m). Melting point (° C.): 71-74.

EXAMPLE 399 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylpentadecanoate (Compound No. 1260)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.37 (1H, s), 7.10-7.00 (2H, m),6.87-6.77 (1H, m), 2.66 (2H, t, J=6.4 Hz), 2.12 (3H, s), 1.85-1.65 (3H,m), 1.35-1.18 (22H, m), 0.95-0.82 (3H, m), 0.80-0.50 (4H, m). Meltingpoint (° C.): 35-37.

EXAMPLE 400 6-Chloro-3-phenoxy-5-(trimethylsilyl)-4-pyridazinol(Compound No. 2402)

¹H-NMR (90 MHz, CDCl₃) δ ppm: 12.0 (1H, brs), 7.30-6.81 (5H, m), 0.28(9H, s). Melting point (° C.): 119-120.

EXAMPLE 401 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylcyclobutanecarboxylate (Compound No. 1286)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.38 (1H, s), 7.14-7.05 (2H, m),6.89-6.79 (1H, m), 3.58-3.40 (1H, m), 2.60-1.85 (6H, m), 2.13 (3H, s),1.82-1.67 (1H, m), 0.80-0.67 (2H, m), 0.64-0.53 (2H, m). Appearance:paste state.

EXAMPLE 402 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylcyclohexanecarboxylate (Compound No. 1298)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.37 (1H, s), 7.15-7.05 (2H, m),6.90-6.80 (1H, m), 2.78-2.60 (1H, m), 2.12 (3H, s), 1.90-1.20 (1OH, m),0.80-0.50 (4H, m). Melting point (° C.): oily product.

EXAMPLE 403 3-(2-Isopropylphenoxy)-6-methyl-4-pyridazinol (Compound No.2418)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.40-7.35 (1H, m), 7.25-7.16 (2H, m),7.04-6.98 (1H, m), 6.43 (1H, s), 3.06 (1H, septet, J=7.0 Hz), 2.36 (3H,s), 1.18 (6H, d, J=7.0 Hz). Melting point (° C.): 259-260.

EXAMPLE 404 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-bromobutanoate (Compound No. 1334)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.44 (1H, s), 7.14-7.05 (2H, m),6.90-6.83 (1H, m), 4.45 (1H, t, J=7.6 Hz), 2.22 (1H, dq, J=7.3, 7.6 Hz),2.13 (3H, s), 1.81-1.69 (1H, m), 1.17 (3H, t, J=7.3 Hz), 0.74-0.69 (2H,m), 0.58-0.56 (2H, m). Appearance: paste state.

EXAMPLE 405 3-(2-Isopropylphenoxy)-6-(trifluoromethyl)-4-pyridazinol(Compound No. 2431)

¹H-NMR (60 MHz, CDCl₃) δ ppm: 7.60-6.70 (4H, m), 6.87 (1H, s), 2.97 (1H,septet, J=7.0 Hz), 1.10 (6H, d, J=7.0 Hz). Melting point (° C.): 126.5.

EXAMPLE 406 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-chlorobutanoate (Compound No. 1340)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.40 (1H, s), 7.14-7.05 (2H, m),6.89-6.82 (1H, m), 3.68 (2H, t, J=6.2 Hz), 2.91 (2H, t, J=7.0 Hz),2.31-2.18 (2H, m), 2.11 (3H, s), 1.79-1.65 (1H, m), 0.80-0.67 (2H, m),0.63-0.53 (2H, m). Appearance: paste state.

EXAMPLE 407 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-methyl-2-butenoate (Compound No. 1358)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.44 (1H, s), 7.12-7.05 (2H, m),6.88-6.80 (1H, m), 5.99-5.97 (1H, m), 2.26 (3H, d, J=1.1 Hz), 2.13 (3H,s) 2.04 (3H, d, J=1.1 Hz), 1.83-1.70 (1H, m), 0.77-0.64 (2H, m),0.60-0.53 (2H, m). Appearance: paste state.

EXAMPLE 408 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl(2E)-3-phenyl-2-propenoate (Compound No. 1364)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.96 (1H, d, J=16.0 Hz), 7.63-7.59 (2H,m), 7.53 (1H, s), 7.48-7.43 (3H, m), 7.09-7.05 (2H, m), 6.86-6.81 (1H,m), 6.66 (1H, d, J=16.0 Hz), 2.16 (3H, s), 1.83-1.75 (1H, m), 0.79-0.54(4H, m). Appearance: amorphous.

EXAMPLE 409 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethyl succinate (Compound No. 1382)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.44 (1H, s), 7.08-7.02 (2H, m),6.88-6.74 (1H, m), 3.69 (3H, s), 3.01 (2H, t, J=7.3 Hz), 2.78 (2H, t,J=7.3 Hz), 2.11 (3H, s), 1.85-1.65 (1H, m), 0.80-0.50 (4H, m).Appearance: oily product.

EXAMPLE 410 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-chlorobenzoate (Compound No. 1441)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.14 (1H, d, J=8.8 Hz), 7.58 (1H, s),7.59-7.39 (3H, m), 7.10-7.05 (2H, m), 6.88-6.80 (1H, m), 2.16 (3H, s),1.90-1.70 (1H, m), 0.85-0.50 (4H, m). Appearance: oily product.

EXAMPLE 411 3-(2-Methylphenoxy)-6-(2-thienyl)-4-pyridazinol (CompoundNo. 2478)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56-7.48 (2H, m), 7.21-7.00 (4H, m),6.97-6.90 (1H, m), 6.69 (1H, s), 2.11 (3H, s). Melting point (° C.):86-87.

EXAMPLE 412 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methylbenzoate (Compound No. 1481)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.20 (1H, d, J=7.0 Hz), 7.56 (1H, s),7.52 (1H, d, J=7.7 Hz), 7.40-7.28 (2H, m), 7.10-7.00 (2H, m), 6.90-6.88(1H, m), 2.69 (3H, s), 2.16 (3H, s), 1.90-1.70 (1H, m), 0.82-0.65 (2H,m), 0.65-0.50 (2H, m). Appearance: oily product.

EXAMPLE 413 3,6-Bis(2-methylphenoxy)-4-pyridazinol (Compound No. 2492)

¹H-NMR (60 MHz, DMF-d₇) δ ppm: 7.40-6.90 (8H, m), 5.79 (1H, s), 2.19(6H, brs) Melting point (° C.): 247-250.

EXAMPLE 414 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methoxybenzoate (Compound No. 1522)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.09 (1H, dd, J=7.9, 2.0 Hz) 7.68-7.57(1H, m), 7.59 (1H, s), 7.15-7.03 (4H, m), 6.90-6.82 (1H, m), 3.96 (3H,s), 2.17 (3H, s), 1.96-1.72 (1H, m), 0.78-0.65 (2H, m), 0.65-0.51 (2H,m). Appearance: gum state.

EXAMPLE 415 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-methylbenzoate (Compound No. 1531)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.05-8.00 (2H, m), 7.58 (1H, s),7.55-7.38 (2H, m), 7.10-7.05 (2H, m), 6.88-6.80 (1H, m), 2.46 (3H, s),2.16 (3H, s), 1.90-1.68 (1H, m), 0.80-0.50 (4H, m). Appearance: oilyproduct.

EXAMPLE 416 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-chlorobenzoate (Compound No. 1537)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.16 (2H, d, J=8.8 Hz), 7.59 (1H, s),7.54 (2H, d, J=8.8 Hz), 7.14-7.07 (2H, m), 6.88-6.83 (1H, m), 2.15 (3H,s), 1.84-1.69 (1H, m), 0.80-0.70 (2H, m), 0.62-0.55 (2H, m). Appearance:amorphous.

EXAMPLE 417 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-bromobenzoate (Compound No. 1543)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.07 (2H, d, J=8.6 Hz), 7.70 (2H, d,J=8.6 Hz), 7.59 (1H, s), 7.12-7.03 (2H, m), 6.89-6.82 (1H, m), 2.15 (3H,s), 1.83-1.67 (1H, m), 0.78-0.50 (4H, m). Appearance: amorphous.

EXAMPLE 418 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-iodobenzoate (Compound No. 1549)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.94 (2H, s), 7.93 (1H, m) 7.62 (1H, s),7.29 (1H, s), 7.12-7.09 (2H, m), 6.89-6.87 (1H, m), 2.17 (3H, s),1.84-1.73 (1H, m), 0.79-0.70 (2H, m), 0.62-0.55 (2H, m). Appearance:paste state.

EXAMPLE 419 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methylbenzoate (Compound No. 1566)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.10 (2H, d, J=8.1 Hz), 7.60 (1H, s),7.34 (2H, d, J=8.1 Hz), 7.12-7.03 (2H, m), 6.88-6.81 (1H, m), 2.46 (3H,s), 2.15 (3H, s), 1.85-1.71 (1H, m), 0.78-0.65 (2H, m), 0.62-0.52 (2H,m). Melting point (° C.): 77.5-78.

EXAMPLE 420 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-tert-butylbenzoate (Compound No. 1575)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.15 (2H, d, J=8.8 Hz), 7.59 (1H, s),7.56 (2H, d, J=8.8 Hz), 7.09-7.06 (2H, m), 6.86-6.82 (1H, m), 2.15 (3H,s), 1.37 (9H, s), 1.82-1.73 (1H, m), 0.76-0.69 (2H, m), 0.60-0.56 (2H,m). Melting point (° C.): 139-142.

EXAMPLE 421 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-nitrobenzoate (Compound No. 1593)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.41 (4H, s), 7.61 (1H, s) 7.14-7.08 (2H,m), 6.89-6.83 (1H, m), 2.17 (3H, s), 1.81-1.70 (1H, m), 0.80-0.71 (2H,m), 0.62-0.54 (2H, m). Appearance: amorphous.

EXAMPLE 422 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methoxybenzoate (Compound No. 1599)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.17 (2H, d, J=8.8 Hz), 7.60 (1H, s),7.12-7.04 (2H, m), 7.01 (2H, d, J=8.8 Hz), 6.88-6.82 (1H, m), 3.90 (1H,s), 2.16 (3H, s), 1.85-1.71 (1H, m), 0.78-0.69 (2H, m), 0.60-0.52 (2H,m). Appearance: amorphous.

EXAMPLE 423 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,4-dichlorobenzoate (Compound No. 1616)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.11 (1H, d, J=8.4 Hz), 7.60-7.57 (2H,m), 7.42 (1H, dd, J=8.4, 2.2 Hz), 7.14-7.08 (2H, m), 6.89-6.83 (1H, m),2.15 (3H, s), 1.85-1.72 (1H, m), 0.78-0.67 (2H, m), 0.63-0.54 (2H, m).Appearance: amorphous.

EXAMPLE 424 6-Chloro-3-(2-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl phthalate (CompoundNo. 1620)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.98-7.94 (1H, m), 7.88-7.84 (1H, m),7.81-7.71 (2H, m), 7.57 (1H, s), 7.28-7.17 (6H, m), 7.08-7.03 (1H, m),3.70 (3H, s), 2.26 (3H, s), 2.15 (3H, s). Appearance: amorphous.

EXAMPLE 425 Potassium6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinoate (Compound No.3811)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.05-6.95 (2H, m), 6.83-6.72 (1H, m),6.47 (1H, s), 2.00-1.83 (1H, m), 0.80-0.64 (2H, m), 0.64-0.48 (2H, m).Melting point (° C.): 187-189.

EXAMPLE 426 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H -pyrazol-5-yl isophthalate(Compound No. 1631)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.61 (1H, t, J=1.5 Hz), 8.54-8.47 (1H,m), 8.22-8.16 (1H, m), 7.71 (1H, t, J=8.1 Hz), 7.61 (1H, s), 7.15-6.96(4H, m), 6.89-6.82 (1H, m), 3.67 (3H, s), 2.44 (3H, s), 2.17 (3H, s),1.88-1.72 (1H, m), 0.83-0.71 (2H, m), 0.64-0.53 (2H, m). Appearance:amorphous.

EXAMPLE 427 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-furoate (Compound No. 1643)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.74-7.73 (1H, m), 7.56 (1H, s), 7.50(1H, dd, J=3.7, 0.7 Hz), 7.13-7.04 (2H, m), 6.88-6.81 (1H, m), 6.65-6.63(1H, m), 2.15 (3H, s), 1.85-1.71 (1H, m), 0.78-0.69 (2H, m), 0.62-0.52(2H, m). Appearance: paste state.

EXAMPLE 428 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-thiophenecarboxylate (Compound No. 1649)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.07-8.05 (1H, m), 7.78-7.75 (1H, m),7,58 (1H, s), 7.24-7.20 (1H, m), 7.13-7.06 (2H, m), 6.89-6.83 (1H, m),2.16 (3H, s), 1.83-1.71 (1H, m), 0.80-0.70 (2H, m), 0.65-0.55 (2H, m).Appearance: amorphous.

EXAMPLE 429 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylisobutyl carbonate (Compound No. 1770)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.49 (1H, s), 7.15-7.05 (2H, m),6.89-6.82 (1H, m), 4.13 (2H, d, J=6.6 Hz), 2.14 (3H, s), 2.09 (1H,br.septet, J=7.0 Hz), 1.88-1.68 (1H, m), 1.01 (6H, d, J=7.0 Hz),0.78-0.52 (4H, m). Melting point (° C.): 72-74.

EXAMPLE 430 Allyl6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl carbonate(Compound No. 1811)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.50 (1H, s), 7.15-7.06 (2H, m),6.89-6.82 (1H, m), 6.10-5.90 (1H, m), 5.51-5.35 (2H, m), 4.84-4.80 (2H,m), 2.14 (3H, s), 1.85-1.70 (1H, m), 0.78-0.53 (4H, m). Appearance: oilyproduct.

EXAMPLE 431 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldimethylcarbamate (Compound No. 1891)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56 (1H s), 7.13-7.05 (2H, m), 6.89-6.82(1H, m), 3.16 (3H, s), 3.05 (3H, s), 2.15 (3H, s), 1.85-1.71 (1H, m),0.78-0.54 (4H, m). Melting point (° C.): 136-138.

EXAMPLE 432 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldiethylcarbamate (Compound No. 1911)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.10-7.07 (2H, m),6.87-6.83 (1H, m), 3.48 (2H, q, J=7.3 Hz), 3.41 (2H, q, J=7.0 Hz), 2.15(3H, s), 1.82-1.72 (1H, m), 1.29 (3H, t, J=7.3 Hz), 1.23 (3H, t, J=7.0Hz), 0.74-0.57 (4H, m). Melting point (° C.): 119-121.

EXAMPLE 433 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldiisopropylcarbamate (Compound No. 1920)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.61 (1H, s), 7.10-7.00 (2H, m),6.90-6.85 (1H, m), 4.20-3.90 (2H, m), 2.14 (3H, s), 1.87-1.67 (1H, m),1.45-1.20 (12H, m), 0.80-0.50 (4H, m). Melting point (° C.): 103-105.

EXAMPLE 434 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-thiophenesulfonate (Compound No. 3792)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.89-7.82 (2H, m), 7.58 (1H, s),7.22-7.13 (1H, m), 7.13-7.02 (2H, m), 6.84-6.79 (1H, m), 1.99 (3H, s),1.69-1.53 (1H, m), 0.70-0.48 (4H, m). Appearance: amorphous.

EXAMPLE 435 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethyl(phenyl)carbamate (Compound No. 1946)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.40-7.25 (6H, m), 7.11-7.08 (2H, m),6.87-6.82 (1H, m), 3.42 (3H, br.s), 2.15 (3H, br.s), 1.82-1.68 (1H, m),0.71-0.56 (4H, m). Appearance: amorphous.

EXAMPLE 436 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldiphenylcarbamate (Compound No. 1952)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.45-7.28 (11H, m), 7.16-7.09 (2H, m),6.87-6.82 (1H, m), 2.11 (3H, s), 1.79-1.66 (1H, m), 0.69-0.56 (4H, m).Appearance: amorphous.

EXAMPLE 437 O-[6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]S-methyl thiocarbonate (Compound No. 1958)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.47 (1H, s), 7.13-7.06 (2H, m),6.89-6.83 (1H, m), 2.49 (3H, s), 2.14 (3H, s), 1.83-1.69 (1H, m),0.78-0.65 (2H, m), 0.63-0.55 (2H, m). Appearance: paste state.

EXAMPLE 438 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylethanesulfonate (Compound No. 2034)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.15-7.05 (2H, m),6.92-6.82 (1H, m), 3.58 (2H, q, J=7.4 Hz), 2.15 (3H, s), 1.82-1.68 (1H,m), 1.64 (3H, t, J=7.4 Hz), 0.78-0.52 (4H, m). Melting point (° C.):96-97.

EXAMPLE 439 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-propanesulfonate (Compound No. 2051)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.18-7.05 (2H, m),6.94-6.83 (1H, m), 3.53 (2H, t, J=7.7 Hz), 2.20-2.00 (2H, m), 2.15 (3H,s), 1.82-1.67 (1H, m), 1.15 (3H, t, J=7.7 Hz), 0.80-0.50 (4H, m).Melting point (° C.): 70.5-71.5.

EXAMPLE 440 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-propanesulfonate (Compound No. 2060)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.18-7.07 (2H, m),6.93-6.82 (1H, m), 3.75 (1H, septet, 7.0 Hz), 2.15 (3H, S), 1.85-1.65(1H, m), 1.65 (6H, d, J=7.0 Hz), 0.78-0.50 (4H, m). Appearance: oilyproduct.

EXAMPLE 441 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-octanesulfonate (Compound No. 2066)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.15-7.07 (2H, m),6.89-6.85 (1H, s), 3.60-3.50 (2H, m), 2.15 (3H, s), 2.15-1.98 (2H, m),1.83-1.67 (1H, m), 1.58-1.15 (1OH, m), 0.95-0.83 (3H, m), 0.80-0.68 (2H,m), 0.65-0.55 (2H, m). Appearance: paste state.

EXAMPLE 442 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylchloromethanesulfonate (Compound No. 2072)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.18-7.09 (2H, m),6.92-6.85 (1H, m), 5.02 (2H, s), 2.16 (3H, s), 1.83-1.68 (1H, m),0.80-0.68 (2H, m), 0.65-0.55 (2H, m). Appearance: paste state.

EXAMPLE 443 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,2,2-trifluoroethanesulfonate (Compound No. 2136)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.55 (1H, s), 7.19-7.05 (2H, m), 6.90(1H, dd, J=6.6, 2.9 Hz), 4.39 (2H, q, J=8.2 Hz), 2.15 (3H, s), 1.80-1.65(1H, m), 0.80-0.50 (4H, m). Appearance: amorphous.

EXAMPLE 444 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-chlorobenzenesulfonate (Compound No. 2212)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.01-7.92 (2H, m), 7.62-7.53 (3H, m),7.13-7.00 (2H, m), 6.85-6.77 (1H, m), 2.04 (3H, s), 1.58-1.45 (1H, m),0.70-0.45 (4H, m). Appearance: gum state.

EXAMPLE 445 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-nitrobenzenesulfonate (Compound No. 2300)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.50-8.39 (2H, m), 8.33-8.20 (2H, m),7.59 (1H, s), 7.15-7.00 (2H, m), 6.85-6.75 (1H, m), 1.94 (3H, s),1.65-1.45 (1H, m), 0.75-0.45 (4H, m). Appearance: gum state.

EXAMPLE 446 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methoxybenzenesulfonate (Compound No. 2309)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.99-7.91 (2H, m), 7.61 (1H, s),7.11-6.98 (4H, m), 6.80 (1H, dd, J=2.6 Hz, 6.6 Hz), 3.90 (3H, s), 1.95(3H, s), 1.60-1.45 (1H, m), 0.70-0.45 (4H, m). Appearance: caramel-like.

EXAMPLE 447 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,4,6-trimethylbenzenesulfonate (Compound No. 2315)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.13-6.98 (4H, m),6.85-6.75 (1H, m), 2.70 (6H, s), 2.32 (3H, s), 2.04 (3H, s), 1.65-1.45(1H, m), 0.78-0.44 (4H, m). Appearance: amorphous.

EXAMPLE 448 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,4,6-triisopropylbenzenesulfonate (Compound No. 2321)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.52 (1H, s), 7.28-7.20 (2H, m),7.10-6.98 (2H, m), 6.85-6.75 (1H, m), 4.16 (2H, septet, J=6.6 Hz), 2.93(1H, septet, J=6.6 Hz), 1.93 (3H, s), 1.75-1.50 (1H, m), 1.35-1.20 (18H,m), 0.75-0.45 (4H, m). Appearance: amorphous.

EXAMPLE 449 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H -pyrazol-5-yl1,2-benzenedisulfonate (Compound No. 2327)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.52-8.40 (1H, m), 8.15-8.07 (1H, m),8.00-7.82 (2H, m), 7.63 (1H, s), 7.18 (2H, s), 7.15-6.97 (3H, m), 6.79(1H, dd, J=7.0, 2.6 Hz), 3.84 (3H, s), 2.11 (3H, s), 1.99 (3H, s),1.75-1.57 (1H, m), 0.74-0.45 (4H, m). Appearance: caramel-like.

EXAMPLE 450 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-chloro-3-nitrobenzenesulfonate (Compound No. 3786)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.55 (1H, d, J=2.2 Hz), 8.18 (1H, dd,J=8.8, 2.2 Hz), 7.81 (1H, d, J=8.8 Hz), 7.59 (1H, s), 7.13-7.06 (2H, m),6.84-6.79 (1H, m), 1.98 (3H, s), 1.61-1.48 (1H, m), 0.68-0.52 (4H, m).Appearance: amorphous.

EXAMPLE 4516-Chloro-3-[2-(2-chloro-2-fluorocyclopropyl)phenoxy]-4-pyridazinol(Compound No. 2519)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.42-7.15 (4H, m), 6.70 (1H, s),2.80-2.62 (1H, m), 2.18-1.65 (2H, m). Melting point (° C.): 175-177.

EXAMPLE 452 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,5-dichlorobenzenesulfonate (Compound No. 3780)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.09-8.08 (1H, m), 7.61-7.52 (3H, m),7.12-7.01 (2H, m), 6.81-6.76 (1H, m), 1.98 (3H, s), 1.67-1.49 (1H, m),0.82-0.60 (2H, m), 0.58-0.48 (2H, m). Appearance: amorphous.

EXAMPLE 453 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl10H-phenothiazine-10-carboxylate (Compound No. 3720)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.76-7.67 (3H, m), 7.49-7.40 (3H, m),7.40-7.23 (3H, m), 7.20-7.10 (2H, m), 6.95-6.83 (1H, m), 2.19 (3H, s),1.88-1.70 (1H, m), 0.85-0.57 (4H, m). Appearance: amorphous.

EXAMPLE 454 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl9H-carbazole-9-carboxylate (Compound No. 3714)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.40 (2H, d, J=7.4 Hz), 8.02 (2H, d,J=7.0 Hz), 7.99 (1H, s), 7.60-7.35 (4H, m), 7.13-7.03 (2H, m), 6.92-6.80(1H, m), 2.19 (3H, s), 1.90-1.73 (1H, m), 0.84-0.50 (4H, m). Meltingpoint (° C.): 157-159.

EXAMPLE 455 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,4-dihydro-2(1H)-isoquinolinecarboxylate (Compound No. 3708)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.32-7.02 (6H, m),6.90-6.78 (1H, m), 4.86 (1H, s), 4.72 (1H, s), 3.92 (1H, t, J=5.9 Hz),3.81 (1H, t, J=5.9 Hz), 3.05-2.95 (2H, m), 2.14 (3H, s), 1.86-1.67 (1H,m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 456 3-[3-(Benzyloxy)phenoxy]-6-chloro-4-pyridazinol (CompoundNo. 2547)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.48-7.25 (6H, m), 6.94-6.66 (4H, m),5.07 (2H, s). Melting point (° C.): 184-185.

EXAMPLE 457 3-[4-(Benzyloxy)phenoxy]-6-chloro-4-pyridazinol (CompoundNo. 2548)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.48-7.28 (5H, m), 7.12-6.96 (4H, m),6.58 (1H, s), 5.07 (2H, s). Melting point (° C.): 170-180.

EXAMPLE 458 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-thiomorpholinecarboxylate (Compound No. 3702)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.53 (1H, s), 7.15-7.04 (2H, m),6.92-6.80 (1H, m), 4.05-3.78 (4H, m), 2.75-2.64 (4H, m), 2.13 (3H, s),1.85-1.65 (1H, m), 0.80-0.54 (4H, m). Appearance: caramel-like.

EXAMPLE 459 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,6-dimethyl-4-morpholinecarboxylate (Compound No. 3696)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.54 (1H, s), 7.18-7.05 (2H, m),6.94-6.80 (1H, m), 4.17-3.97 (2H, m), 3.78-3.55 (2H, m), 2.95-2.60 (2H,m), 2.14 (3H, s), 1.85-1.67 (1H, m), 1.35-1.15 (6H, m), 0.80-0.54 (4H,m). Appearance: caramel-like.

EXAMPLE 460 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-morpholinecarboxylate (Compound No. 3690)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.13-7.06 (2H, m),6.90-6.83 (1H, m), 3.70-3.55 (8H, m), 2.14 (3H, s), 1.83-1.68 (1H, m),0.80-0.65 (2H, m), 0.65-0.53 (2H, m). Melting point (° C.): 102.5-103.5.

EXAMPLE 461 6-Chloro-3-[(1-methyl-1H-indol-4-yl)oxy]-4-pyridazinol(Compound No. 2565)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.29 (1H, d, J=8.4 Hz), 7.17 (1H, t,J=7.7 Hz), 7.13 (1H, d, J=2.9 Hz), 6.85 (1H, d, J=7.7 Hz), 6.72 (1H, s),6.23 (1H, d, J=2.9 Hz), 4.87 (3H, s). Melting point (° C.): 203-206.

EXAMPLE 462 6-Chloro-3-[(1-methyl-1H-indol-7-yl)oxy]-4-pyridazinol(Compound No. 2568)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.42 (1H, d, J=7.0 Hz), 7.07 (1H, d,J=2.9 Hz), 6.99 (1H, t, J=7.7 Hz), 6.86 (1H, d, J=6,6 Hz), 6.74 (1H, s),6.44 (1H, d, J=2.9 Hz), 3.80 (3H, s). Melting point (° C.): 219-221.

EXAMPLE 4631-{4-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-3-methylphenyl}ethanone(Compound No. 2570)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.94-7.86 (2H, m), 7.21-7.16 (1H, m),6.75 (1H, s), 2.60 (3H, s), 2.25 (3H, s). Melting point (° C.): 182-184.

EXAMPLE 4641-{4-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-3-methylphenyl}ethanoneO-methyloxime (Compound No. 2571)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.59-7.51 (2H, m), 7.11-7.06 (1H, m),6.71 (1H, s), 3.95 (3H, s), 2.20 (3H, s). Melting point (° C.): 189-192.

EXAMPLE 465 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-phenyl-1-piperazinecarboxylate (Compound No. 3684)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.60 (1H, s), 7.35-7.23 (2H, m),7.13-7.04 (2H, m), 7.00-6.80 (4H, m), 3.95-3.84 (2H, m), 3.84-3.72 (2H,m), 3.31-3.18 (4H, m), 2.15 (3H, s), 1.86-1.66 (1H, m), 0.80-0.53 (4H,m). Appearance: caramel-like.

EXAMPLE 4664-{[4-(Benzoyloxy)-6-chloro-3-pyridazinyl]oxy}-3-methylphenyl benzoate(Compound No. 3850)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.21-8.17 (4H, m), 7.72-7.48 (7H, m),7.22-7.07 (3H, m), 2.21 (3H, s). Melting point (° C.): 118-120.

EXAMPLE 467 Methyl3-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]-4-methoxybenzoate (CompoundNo. 2574)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.95 (1H, dd J=8.6, 2.2 Hz), 7.78 (1H, d,J=1.8 Hz), 7.19 (1H, d, J=8.8 Hz), 6.71 (1H, s), 3.87 (3H, s), 3.84 (3H,s). Melting point (° C.): 115-123.

EXAMPLE 468 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methyl-1-piperazinecarboxylate (Compound No. 3678)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.15-7.04 (2H, m),6.90-6.80 (1H, m), 3.80-3.55 (4H, m), 2.54-2.40 (4H, m), 2.32 (3H, s),2.14 (3H, s), 1.85-1.67 (1H, m), 0.80-0.52 (4H, m). Appearance:caramel-like.

EXAMPLE 469 6-Chloro-3-(2-isopropenyl-6-methylphenoxy)-4-pyridazinol(Compound No. 2577)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.20-7.10 (3H, m), 6.66 (1H, s), 5.01(1H, m), 4.95 (1H, m), 2.15 (3H, s), 1.99 (3H, s). Melting point (° C.):183-186.

EXAMPLE 4706-Chloro-3-[(1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)oxy-4-pyridazinol(Compound No. 2585)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.15 (1H, d, J=8.1 Hz), 6.95 (2H, br.d,J=8.1 Hz), 6.68 (1H, s), 2.89 (2H, t, J=7.3 Hz), 1.96 (2H, t, J=7.3 Hz),1.27 (6H, s). Melting point (° C.): 209-212.

EXAMPLE 4713-(3-Bromo-6-cyclopropyl-2-methylphenoxy)-6-chloro-4-pyridazinol(Compound No. 2587)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.38 (1H, d, J=8.4 Hz), 6.78 (1H, d,J=8.4 Hz), 6.72 (1H, s), 2.22 (3H, s), 1.85-1.72 (1H, m), 0.85-0.72 (2H,m), 0.65-0.50 (2H, m). Melting point (° C.): 234-235.

EXAMPLE 4726-Chloro-3-(6-cyclopropyl-2-methyl-3-nitrophenoxy)-4-pyridazinol(Compound No. 2589)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.80 (1H, d, J=8.4 Hz), 7.02 (1H, d,J=8.4 Hz), 6.77 (1H, s), 2.32 (3H, s), 1.99-1.88 (1H, m), 0.95-0.88 (2H,m), 0.74-0.70 (2H, m). Melting point (° C.): 140-143.

EXAMPLE 4736-Chloro-3-[(5-methyl-1,3-dihydro-2-benzofuran-4-yl)oxy]-4-pyridazinol(Compound No. 2592)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.20 (1H, d, J=7.7 Hz), 7.08 (1H, d,J=7.7 Hz), 5.06 (2H, br.s), 4.88 (2H, br.s), 2.16 (3H, s). Melting point(° C.): 188-200.

EXAMPLE 474 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,2,6,6-tetramethyl-1-piperidinecarboxylate (Compound No. 3672)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7,53 (1H, s), 7.14-7.03 (2H, m),6.90-6.78 (1H, m), 2.13 (3H, s), 1.90-1.62 (7H, m), 1.55 (12H, s),0.80-0.52 (4H, m). Appearance: caramel-like.

EXAMPLE 475 6-Chloro-3-(2-fluoro-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 2597)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.92 (1H, d, J=7.0 Hz), 6.73 (1H, s),2.24 (3H, s), 2.21 (3H, s), 2.06 (3H, s). Melting point (° C.): 258-260.

EXAMPLE 476 6-Chloro-3-(2-chloro-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 2599)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 7.11 (1H, s), 6.86 (1H, br.s), 2.29(3H, s), 2.24 (3H, s), 1.99 (3H, s). Melting point (° C.): 298-300.

EXAMPLE 477 6-Chloro-3-(2-iodo-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 2600)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.06 (1H, s), 6.75 (1H, s) 2.40 (3H, s),2.26 (3H, s), 2.09 (3H, s). Melting point (° C.): 235 (decomposed).

EXAMPLE 478 6-Chloro-3-(2-ethyl-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 2601)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 6.95 (1H, s), 6.81 (1H, br.s), 2.32(2H, q, J=7.5 Hz), 2.24 (3H, s), 2.12 (3H, s), 1.94 (3H, s), 1.04 (3H,t, J=7.5 Hz). Melting point (° C.): 188-195.

EXAMPLE 479 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1,4-dioxa-8-azaspiro[4.5]decan-8-carboxylate (Compound No. 3666)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.15-7.04 (2H, m),6.92-6.80 (1H, m), 3.99 (4H, s), 3.85-3.62 (4H, m), 2.14 (3H, s),1.85-1.65 (5H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 4806-Chloro-3-(2-isopropenyl-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 2605)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.91 (1H, s), 6.58 (1H, s), 5.00-4.90(2H, bm), 2.27 (3H, s), 2.20 (3H, s), 2.07 (3H, s), 1.96 (3H, s).Appearance: amorphous.

EXAMPLE 481 1-[6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]4-ethyl 1,4-piperidinedicarboxylate (Compound No. 3660)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56 (1H, s) 7.13-7.04 (2H, m), 6.90-6.80(1H, m), 4.30-4.00 (2H, m), 3.35-3.02 (2H, m), 2.65-2.45 (1H, m), 2.14(3H, s), 2.10-1.93 (3H, m), 1.93-1.65 (4H, m), 1.25 (3H, t, J=7.0 Hz),0.80-0.54 (4H, m). Appearance: caramel-like.

EXAMPLE 4821-{2-[(6-Chloro-4-hydroxy3-pyridazinyl)oxy]-3,4,6-trimethylphenyl}ethanone(Compound No. 2607)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.55 (1H, s), 6.72 (1H, s) 2.45 (3H, s),2.36 (3H, s), 2.29 (3H, s), 2.11 (3H, s). Appearance: amorphous.

EXAMPLE 483 6-Chloro-3-(2,3,5-trimethyl-6-nitrophenoxy)-4-pyridazinol(Compound No. 2608)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.11 (1H, s), 6.65 (1H, s), 2.33 (3H, s),2.28 (3H, s), 2.05 (3H, s). Melting point (° C.): 172-174.

EXAMPLE 4846-Chloro-3-(2,4-dichloro-3,5,6-trimethylphenoxy)-4-pyridazinol (CompoundNo. 2609)

¹H-NMR (200 MHz, DMSO-d₆) δ ppm: 6.91 (1H, s), 2.46 (3H, s), 2.36 (3H,s), 2.10 (3H, s).

EXAMPLE 485 6-Chloro-3-(2,3,4,5,6-pentamethylphenoxy)-4-pyridazinol(Compound No. 2614)

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.69 (1H, s), 2.23 (3H, s), 2.21 (6H, s),2.02 (6H, s). Melting point (° C.): 238-240 (decomposed).

EXAMPLE 486 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,3-dimethylbutanoate (Compound No. 2662)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.37 (1H, s), 7.13-7.05 (2H, s),6.88-6.82 (1H, s), 2.55 (2H, s), 2.12 (3H, s), 1.82-1.67 (1H, m), 1.15(9H, s), 0.80-0.65 (2H, m), 0.63-0.52 (2H, m). Melting point (° C.):91-92.

EXAMPLE 487 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-adamantanecarboxylate (Compound No. 2671)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.37 (1H, s), 7.12-7.05 (2H, m),6.92-6.80 (1H, m), 2.13 (3H, s), 2.08 (9H, s), 1.76 (7H, br.s),0.85-0.45 (4H, m). Appearance: oily product.

EXAMPLE 488 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methylacrylate (Compound No. 2677)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.48 (1H, s), 7.14-7.05 (2H, m),6.89-6.83 (1H, m), 6.46 (1H, br.s), 5.91 (1H, br.s), 2.13 (3H, s), 2.09(3H, s), 1.81-1.68 (1H, m), 0.78-0.53 (4H, m). Melting point (° C.):98-100.

EXAMPLE 489 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-bromo-2-methylpropanoate (Compound No. 2697)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.47 (1H, s), 7.11-7.08 (2H, m),6.89-6.85 (1H, m), 2.13 (3H, s), 2.10 (6H, s), 1.77-1.69 (1H, m),0.74-0.58 (4H, m). Melting point (° C.): 69-71.

EXAMPLE 490 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-chloro-2,2-dimethylpropanoate (Compound No. 2703)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.43 (1H, s), 7.13-7.05 (2H, m),6.90-6.84 (1H, m), 3.76 (2H, s), 2.13 (3H, s), 1.83-1.65 (1H, m), 1.50(6H, s), 0.85-0.45 (4H, br.s). Melting point (° C.): 112-115.

EXAMPLE 491 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-bromopentanoate (Compound No. 2709)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.83 (1H, s), 7.11-7.05 (2H, m),6.86-6.82 (1H, m), 3.43 (2H, d, J=6.2 Hz), 2.73 (2H, d, J=7.0 Hz), 2.12(3H, s), 2.04-1.93 (4H, m), 1.77-1.69 (1H, m), 0.74-0.56 (4H, m).Appearance: caramel-like.

EXAMPLE 492 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylhydratropate (Compound No. 2715)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.42-7.20 (5H, m), 7.32 (1H, s),7.15-7.02 (2H, m), 6.86-6.75 (1H, m), 4.20-4.00 (1H, m), 2.04 (3H, s),1.66 (3H, d, J=7.0 Hz), 1.70-1.50 (1H, m), 0.70-0.42 (4H, m).Appearance: oily product.

EXAMPLE 493 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl(4-methoxyphenyl)acetate (Compound No. 2721)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.37 (1H, s), 7.27 (2H, d, J=8.2 Hz),7.13-7.05 (2H, m), 6.89-6.80 (3H, m), 3.91 (2H, s), 3.76 (3H, s), 2.07(3H, s), 1.73-1.60 (1H, m), 0.75-0.50 (4H, m). Appearance: paste state.

EXAMPLE 494 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylethyl succinate (Compound No. 2727)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.08-6.92 (2H, m), 6.85-6.68 (1H, m),6.55 (1H, s), 4.14 (2H, br.q, J=7.1 Hz), 3.00 (1H, t, J=7.0 Hz), 2.76(1H, t, J=7.0 Hz), 2.61 (2H, br.s), 1.98 (3H, s), 1.78-1.60 (1H, m),1.25 (3H, t, J=7.1 Hz), 0.75-0.40 (4H, m). Appearance: amorphous.

EXAMPLE 495 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methyl-1-piperidinecarboxylate (Compound No. 3654)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56 (1H, s), 7.14-7.04 (2H, m),6.90-6.80 (1H, m), 4.35-4.10 (2H, m), 3.15-2.80 (2H, m), 2.14 (3H, s),1.85-1.50 (4H, m), 1.35-1.06 (2H, m), 0.96 (3H, d, J=6.2 Hz), 0.80-0.50(4H, m). Appearance: caramel-like.

EXAMPLE 496 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-bromo-1-piperidinecarboxylate (Compound No. 3648)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.55 (1H, s), 7.15-7.04 (2H, m),6.90-6.80 (1H, m), 4.54-4.38 (1H, m), 4.00-3.53 (4H, m), 2.30-1.90 (7H,m), 1.85-1.67 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 497Bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl] succinate(Compound No. 2733)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.32 (2H, s), 7.14-7.03 (4H, m),6.88-6.81 (2H, m), 3.17 (4H, s), 2.10 (6H, s), 1.80-1.65 (2H, m),0.78-0.53 (8H, m). Appearance: caramel-like.

EXAMPLE 498 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethoxyacetate (Compound No. 2752)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.43 (1H, s), 7.15-7.04 (2H, m),6.90-6.82 (1H, m), 4.41 (2H, s), 3.55 (3H, s), 2.12 (3H, s), 1.82-1.67(1H, m), 0.80-0.67 (2H, m), 0.64-0.55 (2H, m). Appearance: paste state.

EXAMPLE 499 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylphenoxyacetate (Compound No. 2758)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.42 (1H, s), 7.29-7.25 (2H, m),7.23-6.96 (5H, m), 6.89-6.83 (1H, m), 5.00 (2H, s), 2.08 (3H, s),1.73-1.64 (1H, m), 0.71-0.54 (4H, m). Appearance: caramel-like.

EXAMPLE 500 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-phenoxypropanoate (Compound No. 2764)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.33 (1H, s), 7.25-7.19 (2H, m),7.17-7.04 (2H, m), 7.00-6.91 (3H, m), 6.86-6.82 (1H, m), 5.09 (1H, q,J=6.6 Hz), 2.05 (3H, s), 1.84 (3H, d, J=6.6 Hz), 1.64-1.58 (1H, m),0.68-0.52 (4H, m). Appearance: caramel-like.

EXAMPLE 501 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethoxy(phenyl)acetate (Compound No. 2770)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56-7.51 (2H, m), 7.40-7.30 (4H, m),7.12-7.02 (2H, m), 6.83-6.78 (1H, m), 5.10 (1H, s), 3.52 (3H, s), 2.01(3H, s), 1.67-1.50 (1H, m), 0.70-0.43 (4H, m). Appearance: paste state.

EXAMPLE 502 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-(methylsulfanyl)propanoate (Compound No. 2776)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.42 (1H, s), 7.10-7.00 (2H, m),6.90-6.77 (1H, m), 3.07-2.83 (4H, m), 2.17 (3H, s), 2.12 (3H, s),1.85-1.65 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 503 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyloxo(2-thienyl)acetate (Compound No. 2782)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.07 (1H, dd, J=1.5 Hz, 4.1 Hz), 7.77(1H, dd, J=1.5 Hz, 4.1 Hz), 7.58 (1H, s), 7.22 (1H, t, J=4.0 Hz),7.10-7.02 (2H, m), 6.90-6.77 (1H, m), 2.15 (3H, s), 1.90-1.70 (1H, m),0.85-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 504 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-fluorobenzoate (Compound No. 2788)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.17-8.09 (1H, m), 7.73-7.62 (1H, m),7.57 (1H, s), 7.36-7.20 (2H, m), 7.09-7.07 (2H, m), 6.87-6.82 (1H, m),2.16 (3H, s), 1.85-1.72 (1H, m), 0.76-0.56 (4H, m). Appearance:amorphous.

EXAMPLE 505 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-bromobenzoate (Compound No. 2805)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.20-8.05 (1H, m), 7.85-7.70 (1H, m),7.59 (1H, s), 7.55-7.38 (2H, m), 7.15-7.00 (2H, m), 6.90-6.80 (1H, m),2.17 (3H, s), 1.88-1.70 (1H, m), 0.80-0.50 (4H, m). Appearance:caramel-like.

EXAMPLE 506 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-iodobenzoate (Compound No. 2814)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.20-8.05 (2H, m), 7.60-7.44 (2H, m),7.35-7.20 (1H, m), 7.13-7.00 (2H, m), 6.90-6.78 (1H, m), 2.17 (3H, s),1.90-1.72 (1H, m), 0.85-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 507 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-(trifluoromethyl)benzoate (Compound No. 2820)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.13-8.09 (1H, m), 7.91-7.86 (1H, m),7.76-7.72 (2H, m), 7.55 (1H, s), 7.11-7.06 (2H, m), 6.88-6.83 (1H, m),2.16 (3H, s), 1.86-1.71 (1H, m), 0.75-0.56 (4H, m). Appearance:caramel-like.

EXAMPLE 508 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-benzylbenzoate (Compound No. 2826)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.22-8.18 (1H, d, J=7.2 Hz) 7.62-7.54(1H, t, J=7.6 Hz), 7.44-7.06 (1OH, m), 6.85-6.81 (1H, m), 4.46 (1H, s),2.11 (3H, s), 1.80-1.67 (1H, m), 0.75-0.64 (2H, m), 0.60-0.52 (2H, m).Appearance: paste state.

EXAMPLE 509 Bis[6-chloro-3-(2-methylphenoxy)-4-pyridazinyl] phthalate(Compound No. 2827)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.06 (2H, dd, J=6.0, 3.4 Hz) 7.57 (2H,s), 7.25-7.15 (8H, m), 7.05-7.01 (2H, m), 2.14 (6H, s). Melting point (°C.): 157-158.

EXAMPLE 510 1-[6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]2-methyl 1,2-piperidinedicarboxylate (Compound No. 3642)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.60 (0.5H, s), 7.59 (0.5H, s), 7.14-7.03(2H, m), 6.92-6.80 (1H, m), 5.10-4.90 (1H, m), 4.32-4.06 (1H, m), 3.73(1.5H, s), 3.71 (1.5H, s), 3.40-3.05 (1H, m), 2.43-2.20 (1H, m), 2.15(1.5H, s), 2.13 (1.5H, s), 2.00-1.20 (6H, m), 0.80-0.50 (4H, m).Appearance: caramel-like.

EXAMPLE 511 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-nitrobenzoate (Compound No. 2850)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.15-8.05 (1H, m), 7.95-7.72 (3H, m),7.65 (1H, s), 7.14-7.05 (2H, m), 6.90-6.80 (1H, m), 2.15 (3H, s),1.85-1.70 (1H, m), 0.78-0.65 (2H, m), 0.65-0.50 (2H, m). Appearance:oily product.

EXAMPLE 512 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-phenoxybenzoate (Compound No. 2856)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.35 (1H, dd, J=8.2, 1.8 Hz), 8.15 (1H,dd, J=8.0, 1.8 Hz), 7.74 (1H, dt, J=7.0, 1.4 Hz), 7.61-7.21 (5H, m),7.15-6.98 (4H, m), 6.84-6.79 (1H, m), 2.09 (3H, s), 1.80-1.68 (1H, m),0.70-0.71 (2H, m), 0.59-0.51 (2H, m). Appearance: paste state.

EXAMPLE 513 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-chlorobenzoate (Compound No. 2868)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.18 (1H, d, J=1.8 Hz), 8.10 (1H, d,J=8.1 Hz), 7.68 (1H, br.d, J=9.2 Hz), 7.57 (1H, s), 7.50 (1H, t, J=8.1Hz), 7.08 (1H, d, J=5.8 Hz), 7.07 (1H, d, J=3.7 Hz), 6.85 (1H, dd,J=5.8, 3.7 Hz), 2.15 (3H, s), 1.85-1.66 (1H, m), 0.80-0.50 (4H, m).Appearance: amorphous.

EXAMPLE 514 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-fluorobenzoate (Compound No. 2862)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.02 (1H, dd, J=6.2, 1.5 Hz), 7.89 (1H,br.d, J=8.8 Hz), 7.60-7.34 (2H, m), 7.59 (1H, s), 7.13-7.04 (2H, m),6.90-6.78 (1H, m), 2.15 (3H, s), 1.83-1.68 (1H, m), 0.80-0.50 (4H, m).Appearance: oily product.

EXAMPLE 515 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-bromobenzoate (Compound No. 2874)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.33 (1H, s), 8.14 (1H, d, J=8.0 Hz),7.82 (1H, d, J=8.0 Hz), 7.56 (1H, s), 7.43 (1H, t, J=8.0 Hz), 7.13-7.03(2H, m), 6.90-6.80 (1H, m), 2.15 (3H, s), 1.85-1.68 (1H, m), 0.80-0.50(4H, m). Appearance: caramel-like.

EXAMPLE 516 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-iodobenzoate (Compound No. 2880)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.54 (1H, d, J=1.8 Hz), 8.20-8.15 (1H,m), 8.03 (1H, d, J=8.1 Hz), 7.56 (1H, s), 7.34-7.26 (1H, m), 7.13-7.05(2H, m), 6.89-6.82 (1H, m), 2.15 (3H, s), 1.83-1.71 (1H, m), 0.80-0.68(2H, m), 0.65-0.52 (2H, m). Appearance: amorphous.

EXAMPLE 517 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-(trifluoromethyl)benzoate (Compound No. 2900)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.47 (1H, s), 8.41 (1H, d, J=7.7 Hz),7.96 (1H, d, J=7.3 Hz), 7.75-7.67 (1H, m), 7.58 (1H, s), 7.12-7.06 (2H,m), 6.89-6.82 (1H, m), 2.16 (3H, s), 1.84-1.71 (1H, m), 0.80-0.53 (4H,m). Appearance: caramel-like.

EXAMPLE 518Bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]isophthalate (Compound No. 2906)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.02 (1H, s), 8.53 (2H, d, J=8.2 Hz),7.78 (1H, t, J=7.8 Hz), 7.58 (2H, s), 7.08-7.06 (4H, m), 6.86-6.82 (2H,m), 2.14 (6H, s), 1.83-1.68 (2H, m), 0.78-0.69 (4H, m), 0.60-0.53 (4H,m). Appearance: paste state.

EXAMPLE 519 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-nitrobenzoate (Compound No. 2918)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.05-9.04 (1H, m), 8.59-8.52 (2H, m),7.79 (1H, t, J=7.7 Hz), 7.59 (1H, s), 7.13-7.07 (2H, m), 6.89-6.82 (1H,m), 2.15 (3H, s), 1.83-1.72 (1H, m), 0.80-0.54 (4H, m). Appearance:caramel-like.

EXAMPLE 520 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-phenoxybenzoate (Compound No. 2924)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.95-7.90 (1H, m), 7.80-7.78 (1H, m),7.57 (1H, s), 7.50 (1H, t, J=8.0 Hz), 7.40-7.30 (3H, m), 7.17-7.10 (1H,m), 7.09-7.03 (3H, m), 7.07 (1H, s), 6.87-6.82 (1H, m), 2.13 (3H, s),1.81-1.67 (1H, m), 0.78-0.66 (2H, m). 0.59-0.54 (2H, m). Appearance:paste state.

EXAMPLE 521 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-fluorobenzoate (Compound No. 2930)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.30-8.18 (2H, m), 7.59 (1H, s),7.30-7.15 (2H, m), 7.15-7.02 (2H, m), 6.90-6.78 (1H, m), 2.15 (3H, s),1.85-1.70 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 522 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-ethylbenzoate (Compound No. 2961)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.13 (2H, d, J=8.5 Hz), 7.60 (1H, s),7.36 (2H, d, J=8.5 Hz), 7.12-7.04 (2H, m), 6.88-6.81 (1H, m), 2.75 (2H,q, J=7.6 Hz), 2.04 (3H, s), 1.85-1.71 (1H, m), 1.28 (3H, t, J=7.6 Hz),0.79-0.65 (2H, m), 0.61-0.52 (2H, m) Appearance: paste state.

EXAMPLE 523 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-propylbenzoate (Compound No. 2970)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.12 (2H, d, J=8.4 Hz), 7.59 (1H, s),7.34 (2H, d, J=8.4 Hz), 7.12-7.05 (2H, m), 6.88-6.81 (1H, m), 2.69 (2H,t, J=7.3 Hz), 2.16 (3H, s), 1.85-1.60 (3H, m), 0.96 (3H, t, J=7.3 Hz),0.80-0.68 (2H, m), 0.63-0.52 (2H, m). Appearance: paste state.

EXAMPLE 524 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-isopropylbenzoate (Compound No. 2976)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.14 (2H, d, J=8.4 Hz), 7.59 (1H, s),7.40 (2H, d, J=8.4 Hz), 7.12-7.05 (2H, m), 6.90-6.82 (1H, m), 3.01 (1H,septet, J=7.0 Hz), 2.15 (3H, s), 1.85-1.70 (1H, m), 1.29 (6H, d, J=7.0Hz), 0.80-0.65 (2H, m), 0.63-0.52 (2H, m). Appearance: paste state.

EXAMPLE 525 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-butylbenzoate (Compound No. 2982)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.12 (2H, d, J=8.1 Hz), 7.59 (1H, s),7.35 (2H, d, J=8.1 Hz), 7.12-7.03 (2H, m), 6.89-6.81 (1H, m), 2.72 (2H,t, J=7.3 Hz), 2.16 (3H, s), 1.85-1.57 (3H, m), 1.47-1.22 (2H, m), 0.94(3H, t, J=7.3 Hz), 0.80-0.68 (2H, m), 0.65-0.55 (2H, m). Appearance:paste state.

EXAMPLE 526 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(trifluoromethyl)benzoate (Compound No. 2988)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.34 (2H, d, J=8.8 Hz), 7.83 (2H, d,J=8.8 Hz), 7.60 (1H, s), 7.14-7.07 (2H, m), 6.89-6.83 (1H, m), 2.15 (3H,s), 1.83-1.72 (1H, m), 0.79-0.71 (2H, m), 0.63-0.54 (2H, m). Meltingpoint (° C.): 127-128.

EXAMPLE 527 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-cyanobenzoate (Compound No. 2994)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.33 (2H, d, J=8.8 Hz), 7.86 (2H, d,J=8.8 Hz), 7.60 (1H, s), 7.14-7.07 (2H, m), 6.89-6.83 (1H, m), 2.14.(3H, s), 1.82-1.68 (1H, m), 0.79-0.53 (4H, m). Appearance: caramel-like.

EXAMPLE 528Bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]terephthalate (Compound No. 3001)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.39 (4H, s), 7.62 (2H, s) 7.10-7.07 (4H,m), 6.87-6.83 (2H, m), 2.15 (6H, s), 1.81-1.68 (2H, m), 0.78-0.70 (4H,m), 0.61-0.53 (4H, m). Melting point (° C.): 247-249.

EXAMPLE 529 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl[1,1′-biphenyl]-4-carboxylate (Compound No. 3016)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.31-8.23 (2H, m), 7.79-7.74 (2H, m),7.67-7.62 (3H, m), 7.54-7.42 (3H, m), 7.09-7.06 (2H, m), 6.87-6.82 (1H,m), 2.17 (3H, s), 1.84-1.75 (1H, m), 0.77-0.56 (4H, m). Melting point (°C.): 135-137.

EXAMPLE 530 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(trifluoromethoxy)benzoate (Compound No. 3022)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.28 (2H, d, J=9.2 Hz), 7.59 (1H, s),7.38 (2H, d, J=9.2 Hz), 7.14-7.04 (2H, m), 6.89-6.82 (1H, m), 2.15 (3H,s), 1.83-1.69 (1H, m), 0.78-0.65 (2H, m), 0.62-0.53 (2H, m) Appearance:paste state.

EXAMPLE 531 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(benzyloxy)benzoate (Compound No. 3028)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.16 (2H, d, J=9.2 Hz), 7.60 (1H, s),7.50-7.30 (5H, m), 7.10-7.03 (4H, m), 6.89-6.82 (1H, m), 5.17 (2H, s),2.15 (3H, s), 1.85-1.72 (1H, m), 0.80-0.68 (2H, m), 0.65-0.53 (2H, m).Appearance: paste state.

EXAMPLE 532 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,3-difluorobenzoate (Compound No. 3034)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.93-7.85 (1H, m), 7.57 (1H, s),7.57-7.44 (1H, m), 7.32-7.21 (1H, m), 7.10-7.05 (2H, m), 6.87-6.82 (1H,m), 2.15 (3H, s), 1.81-1.73 (1H, m), 0.76-0.72 (2H, m), 0.60-0.56 (2H,m). Appearance: paste state.

EXAMPLE 533 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-fluoro-3-(trifluoromethyl)benzoate (Compound No. 3040)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.36-8.28 (1H, m), 7.99-7.92 (1H, m),7.56 (1H, s), 7.49-7.41 (1H, m), 7.13-7.05 (2H, m), 6.89-6.83 (1H, m),2.15 (3H, s), 1.84-1.72 (1H, m), 0.80-0.54 (4H, m). Appearance:amorphous.

EXAMPLE 534 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,3-dimethylbenzoate (Compound No. 3046)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.00-7.96 (1H, m), 7.54 (1H, s),7.45-7.41 (1H, m), 7.27-7.20 (1H, m), 7.14-7.05 (2H, m), 6.89-6.82 (1H,m), 2.57 (3H, s), 2.37 (3H, s), 2.16 (3H, s), 1.86-1.72 (1H, m),0.79-0.69 (2H, m), 0.61-0.53 (2H, m). Appearance: paste state.

EXAMPLE 535 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-chloro-2-methylbenzoate (Compound No. 3052)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.04 (1H, d, J=8.1 Hz), 7.65 (1H, d,J=8.1 Hz), 7.54 (1H, s), 7.33-7.25 (1H, m), 7.13-7.06 (2H, m), 6.89-6.83(1H, m), 2.73 (3H, s), 2.15 (3H, s), 1.83-1.71 (1H, m), 0.79-0.68 (2H,m), 0.65-0.53 (2H, m). Appearance: amorphous.

EXAMPLE 536 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,4-difluorobenzoate (Compound No. 3058)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.23-8.12 (1H, m), 7.56 (1H, s),7.10-6.94 (4H, m), 6.87-6.82 (1H, m), 2.15 (3H, s), 1.81-1.73 (1H, m),0.75-0.56 (4H, m). Appearance: amorphous.

EXAMPLE 537 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-chloro-2-fluorobenzoate (Compound No. 3064)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.07 (1H, dd, J=7.4 Hz, 8.5 Hz), 7.55(1H, s), 7.38-7.22 (2H, m), 7.14-7.03 (2H, m), 6.90-6.78 (1H, m), 2.15(3H, s), 1.85-1.68 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 538 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-fluoro-4-(trifluoromethyl)benzoate (Compound No. 3070)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.30-8.22 (1H, m), 7.61-7.52 (2H, m),7.57 (1H, s), 7.14-7.05 (2H, m), 6.87-6.82 (1H, m), 2.15 (3H, m),1.83-1.69 (1H, m), 0.78-0.70 (2H, m), 0.65-0.55 (2H, m). Appearance:paste state.

EXAMPLE 539 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-chloro-4-fluorobenzoate (Compound No. 3076)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.25-8.18 (1H, m), 7.57 (1H, s),7.34-7.29 (1H, m), 7.19-7.05 (3H, m), 6.89-6.82 (1H, m), 2.15 (3H, m),1.84-1.70 (1H, m), 0.79-0.68 (2H, m), 0.64-0.53 (2H, m). Appearance:paste state.

EXAMPLE 540 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-bromo-2-chlorobenzoate (Compound No. 3082)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.01 (1H, d, J=8.4 Hz), 7.76 (1H, d,J=1.8 Hz), 7.60-7.55 (2H, m), 7.10-7.07 (2H, m), 6.87-6.83 (1H, m), 2.15(3H, s), 1.83-1.71 (1H, m), 0.77-0.71 (2H, m), 0.62-0.56 (2H, m).Appearance: paste state.

EXAMPLE 541 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-bromo-2-methylbenzoate (Compound No. 3088)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.05 (1H, d, J=8.4 Hz), 7.56-7.48 (3H,m), 7.09-7.07 (2H, m), 6.86-6.82 (1H, m), 2.14 (3H, s), 2.04 (3H, s),1.85-1.72 (1H, m), 0.79-0.71 (2H, m), 0.64-0.55 (2H, m). Appearance:paste state.

EXAMPLE 542 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,4-dimethylbenzoate (Compound No. 3094)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.11 (1H, d, J=8.9 Hz), 7.57 (1H, s),7.16-7.13 (2H, m), 7.09-7.05 (2H, m), 6.88-6.81 (1H, m), 2.65 (3H, s),2.41 (3H, s), 2.15 (3H, s), 1.85-1.71 (1H, m), 0.80-0.68 (2H, m),0.67-0.55 (2H, m). Appearance: paste state.

EXAMPLE 543 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,5-dichlorobenzoate (Compound No. 3100)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.10 (1H, d, J=2.2 Hz), 7.60-7.45 (3H,m), 7.15-7.04 (2H, m), 6.90-6.78 (1H, m), 2.15 (3H, s), 1.85-1.70 (1H,m), 0.80-0.50 (4H, m). Melting point (° C.): 128-130.

EXAMPLE 544 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-bromo-2-chlorobenzoate (Compound No. 3106)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.20 (1H, d, J=2.2 Hz), 7.68 (1H, dd,J=2.2 Hz, 8.4 Hz), 7.54 (1H, s), 7.43 (1H, d, J=8.4 Hz), 7.14-7.03 (2H,m), 6.92-6.80 (1H, m), 2.15 (3H, s), 1.87-1.70 (1H, m), 0.85-0.50 (4H,m). Appearance: caramel-like.

EXAMPLE 545 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-bromo-5-methoxybenzoate (Compound No. 3112)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.67-7.57 (3H, m), 7.12-7.00 (3H, m),6.87-6.82 (1H, m), 3.85 (3H, s), 2.16 (3H, s), 1.87-1.75 (1H, m),0.80-0.68 (2H, m), 0.65-0.55 (2H, m). Appearance: paste state.

EXAMPLE 546 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,5-dimethylbenzoate (Compound No. 3129)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.99 (1H, s), 7.54 (1H, s) 7.37-7.30 (1H,m), 7.25-7.21 (1H, m), 7.13-7.05 (2H, m), 6.89-6.82 (1H, m), 2.63 (3H,s), 2.40 (3H, s), 2.16 (3H, s), 1.86-1.72 (1H, m), 0.80-0.70 (2H, m),0.62-0.54 (2H, m). Appearance: oily product.

EXAMPLE 547 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,6-difluorobenzoate (Compound No. 3138)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.68-7.50 (2H, m), 7.15-7.00 (4H, m),6.90-6.77 (1H, m), 2.15 (3H, s), 1.90-1.70 (1H, m), 0.85-0.50 (4H, m).Appearance: caramel-like.

EXAMPLE 548 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-chloro-6-fluorobenzoate (Compound No. 3144)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.57-7.00 (5H, m),6.90-6.78 (1H, m), 2.16 (3H, s), 1.90-1.75 (1H, m), 0.80-0.50 (4H, m).Appearance: caramel-like.

EXAMPLE 549 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,6-dichlorobenzoate (Compound No. 3150)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.43-7.41 (3H, m),7.11-7.08 (2H, m), 6.88-6.83 (1H, m), 2.17 (3H, s), 1.85-1.77 (1H, m),0.74-0.56 (4H, m). Appearance: amorphous.

EXAMPLE 550 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,6-dimethylbenzoate (Compound No. 3156)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.48 (1H, s), 7.32 (1H, dd, J=8.4, 7.0Hz), 7.15-7.07 (3H, m), 6.87-6.83 (1H, m), 2.53 (6H, s), 2.16 (3H, s),1.84-1.76 (1H, m), 0.75-0.69 (2H, m), 0.62-0.57 (2H, m). Appearance:paste state.

EXAMPLE 551 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,6-dimethoxybenzoate (Compound No. 3162)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.39 (1H, t, J=8.8 Hz),7.09-7.07 (2H, m), 6.85-6.81 (1H, m), 6.62 (2H, d, J=6.6 Hz), 3.84 (6H,s), 2.17 (3H, s), 1.96-1.81 (1H, m), 0.74-0.55 (4H, m). Melting point (°C.): 127-128.

EXAMPLE 552 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,4-difluorobenzoate (Compound No. 3168)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.10-7.99 (2H, m), 7.58 (1H, s),7.43-7.25 (1H, m), 7.15-7.02 (2H, m), 6.90-6.80 (1H, m), 2.15 (3H, s),1.83-1.67 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 553 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-fluoro-4-methylbenzoate (Compound No. 3185)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.90 (1H, d, J=8.1 Hz), 7.83 (1H, d,J=9.9 Hz), 7.59 (1H, s), 7.37 (1H, dd, J=7.3 Hz, 7.7 Hz), 7.15-7.00 (2H,m), 6.90-6.78 (1H, m), 2.39 (3H, d, 1.5 Hz), 2.15 (3H, s), 1.85-1.67(1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 554 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,4-dichlorobenzoate (Compound No. 3194)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.29 (1H, d, J=1.8 Hz), 8.03 (1H, dd,J=8.4, 2.2 Hz), 7.65 (1H, d, J=8.4 Hz), 7.57 (1H, s), 7.15-7.02 (2H, m),6.90-6.80 (1H, m), 2.15 (3H, s), 1.82-1.68 (1H, m), 0.78-0.47 (4H, m).Appearance: amorphous.

EXAMPLE 555 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-chloro-3-nitrobenzoate (Compound No. 3200)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.69 (1H, d, J=1.8 Hz), 8.33 (1H, dd,J=8.4, 1.8 Hz), 7.78 (1H, d, J=8.4 Hz), 7.57 (1H, s), 7.10-7.05 (2H, m),6.87-6.82 (1H, m), 2.14 (3H, s), 1.77-1.69 (1H, m), 0.75-0.56 (4H, m).Appearance: amorphous.

EXAMPLE 556 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,5-difluorobenzoate (Compound No. 3217)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.80-7.65 (2H, m), 7.58 (1H, s),7.32-7.00 (3H, m), 6.90-6.80 (1H, m), 2.15 (3H, s), 1.85-1.65 (1H, m),0.80-0.50 (4H, m). Appearance: amorphous.

EXAMPLE 557 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,5-dichlorobenzoate (Compound No. 3226)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.07 (2H, d, J=2.0 Hz), 7.69 (1H, t,J=2.0 Hz), 7.55 (1H, s), 7.13-7.00 (2H, m), 6.89-6.82 (1H, m), 2.15 (3H,s), 1.83-1.60 (1H, m), 0.80-0.70 (2H, m), 0.63-0.55 (2H, m). Meltingpoint (° C.): 168-174.

EXAMPLE 558 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,5-dimethylbenzoate (Compound No. 3243)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.82 (2H, s), 7.56 (1H, s) 7.32 (1H, s,),7.13-7.04 (2H, m), 6.89-6.82 (1H, m), 2.41 (6H, s), 2.16 (3H, s),1.85-1.72 (1H, m), 0.80-0.70 (2H, m), 0.63-0.53 (2H, m). Melting point(° C.): 117-119.

EXAMPLE 559 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,5-dimethoxybenzoate (Compound No. 3252)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.34 (1H, s) 7.33 (1H, s),7.08-7.06 (2H, m), 6.87-6.82 (1H, m), 6.78-6.75 (1H, m), 3.86 (6H, s),2.16 (3H, s), 1.86-1.72 (1H, m), 0.80-0.72 (2H, m), 0.63-0.54 (2H, m).Appearance: paste state.

EXAMPLE 560 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,4,6-trichlorobenzoate (Compound No. 3258)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.55 (1H, s), 7.46 (2H, s) 7.15-7.05 (2H,m), 6.90-6.82 (1H, m), 2.16 (3H, s), 1.86-1.72 (1H, m), 0.78-0.67 (2H,m), 0.65-0.55 (2H, m). Appearance: paste state.

EXAMPLE 561 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3,4,5-trimethoxybenzoate (Compound No. 3264)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.45 (2H, s), 7.14-7.04(2H, m), 6.89-6.83 (1H, m), 3.96 (3H, s), 3.94 (6H, s), 2.16 (3H, s),1.85-1.72 (1H, m), 0.80-0.67 (2H, m), 0.63-0.54 (2H, m). Appearance:amorphous.

EXAMPLE 562 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-naphthoate (Compound No. 3270)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.02 (1H, d, J=8.4 Hz), 8.55 (1H, d,J=7.3 Hz), 8.17 (1H, d, J=8.0 Hz), 7.95 (1H, d, J=8.0 Hz), 7.75-7.54(4H, m), 7.13-7.00 (2H, m), 6.90-6.80 (1H, m), 2.18 (3H, s), 1.93-1.75(1H, m), 0.83-0.52 (4H, m). Appearance: amorphous.

EXAMPLE 563 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-naphthoate (Compound No. 3276)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.81 (1H, s), 8.18 (1H, dd, J=1.5 Hz, 8.5Hz), 8.05-7.87 (3H, m), 7.70-7.52 (3H, m), 7.10-7.00 (2H, m), 6.90-6.77(1H, m), 2.18 (3H, s), 1.90-1.73 (1H, m), 0.83-0.53 (4H, m). Appearance:amorphous.

EXAMPLE 564 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-methyl-1H-pyrrole-2-carboxylate (Compound No. 3282)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.25 (1H, s), 7.08-7.06(2H, m), 6.96 (1H, s), 6.86-6.81 (1H, m), 6.24-6.21 (1H, m), 3.97 (3H,s), 2.15 (3H, s), 1.87-1.72 (1H, m), 0.80-0.70 (2H, m), 0.63-0.52 (2H,m). Melting point (° C.): 143-144.

EXAMPLE 565 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-bromo-2-furoate (Compound No. 3288)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.53 (1H, s), 7.43 (1H, d, J=3.7 Hz),7.15-7.03 (2H, m), 6.90-6.78 (1H, m), 6.59 (1H, d, J=3.7 Hz), 2.15 (3H,s), 1.83-1.70 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 566 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-furoate (Compound No. 3294)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.30 (1H, t, J=0.7 Hz), 7.57-7.53 (1H,m), 7.55 (1H, s), 7.13-7.04 (2H, m), 6.92-6.81 (2H, m), 2.15 (3H, s),1.83-1.69 (1H, s), 0.80-0.53 (4H, m). Appearance: paste state.

EXAMPLE 567 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-tert-butyl-2-methyl-3-furoate (Compound No. 3300)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.09-7.07 (2H, m),6.87-6.83 (1H, m), 6.33 (1H, s), 2.64 (3H, s), 2.15 (3H, s), 1.78-1.73(1H, m), 1.29 (9H, s), 0.75-0.57 (4H, m). Appearance: caramel-like.

EXAMPLE 568 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-methyl-2-(trifluoromethyl)-3-furoate (Compound No. 3306)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.53 (1H, s), 7.13-7.04 (2H, m),6.89-6.82 (1H, m), 6.64 (1H, s), 2.42 (3H, s), 2.13 (3H, s), 1.81-1.67(1H, m), 0.78-0.68 (2H, m), 0.65-0.53 (2H, m). Appearance: paste state.

EXAMPLE 569 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-(4-chlorophenyl)-2-(trifluoromethyl)-3-furoate (Compound No. 3312)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.70-7.66 (2H, m), 7.56 (1H, s),7.47-7.42 (2H, m), 7.19 (1H, s), 7.14-7.05 (2H, m), 6.90-6.82 (1H, m),2.14 (3H, s), 1.83-1.69 (1H, m), 0.80-0.68 (2H, m), 0.65-0.53 (2H, m).Appearance: paste state.

EXAMPLE 570 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-chloro-2-thiophenecarboxylate (Compound No. 3318)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.68 (1H, d, J=5.5 Hz), 7.58 (1H, s),7.14 (1H, d, J=5.5 Hz), 7.11-7.03 (2H, m), 6.90-6.80 (1H, m), 2.16 (3H,s), 1.85-1.70 (1H, m), 0.85-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 571 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-methyl-2-thiophenecarboxylate (Compound No. 3324)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.65-7.55 (2H, m), 7.13-6.95 (3H, m),6.90-6.80 (1H, m), 2.63 (3H, s), 2.16 (3H, s), 1.90-1.70 (1H, m),0.85-0.50 (4H, m). Appearance: amorphous.

EXAMPLE 572 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-ethoxy-2-thiophenecarboxylate (Compound No. 3330)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.62 (1H, s), 7.59 (1H, d, J=5.5 Hz),7.08-7.06 (2H, m), 6.90 (1H, d, J=5.5 Hz), 6.86-6.81 (1H, m), 4.26 (2H,q, J=7.0 Hz), 2.17 (3H, s), 1.86-1.75 (1H, m), 1.46 (3H, t, J=7.0 Hz),0.75-0.55 (4H, m). Appearance: caramel-like.

EXAMPLE 573 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-chloro-2-thiophenecarboxylate (Compound No. 3336)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.86 (1H, d, J=4.0 Hz), 7.57 (1H, s),7.14-7.03 (3H, m), 6.90-6.83 (1H, m), 2.15 (3H, m), 1.83-1.68 (1H, m),0.80-0.68 (2H, m), 0.65-0.53 (2H, m). Appearance: paste state.

EXAMPLE 574 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-bromo-2-thiophenecarboxylate (Compound No. 3342)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.80 (1H, d, J=4.0 Hz), 7.57 (1H, s),7.19 (1H, d, J=4.0 Hz), 7.10-7.00 (2H, m), 6.90-6.80 (1H, m), 2.15 (3H,s), 1.85-1.65 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 575 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-methyl-2-thiophenecarboxylate (Compound No. 3348)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.87 (1H, d, J=3.7 Hz), 7.57 (1H, s),7.12-7.00 (2H, m), 6.93-6.87 (2H, m), 2.58 (3H, s), 2.15 (3H, s),1.85-1.70 (1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 576 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-acetyl-2-thiophenecarboxylate (Compound No. 3354)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.02 (1H, d, J=4.0 Hz), 7.72 (1H, d,J=4.0 Hz), 7.58 (1H, s), 7.10-7.07 (2H, m), 6.87-6.83 (1H, m), 2.63 (3H,s), 2.15 (3H, s), 1.79-1.71 (1H, m), 0.75-0.56 (4H, m). Appearance:amorphous.

EXAMPLE 577 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-nitro-3-thiophenecarboxylate (Compound No. 3360)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.52 (1H, d, J=1.8 Hz), 8.43 (1H, d,J=1.8 Hz), 7.56 (1H, s), 7.13-7.05 (2H, m), 6.90-6.80 (1H, m), 2.14 (3H,s), 1.85-1.65 (1H, m), 0.85-0.50 (4H, m). Appearance: amorphous.

EXAMPLE 578 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4,5-dibromo-2-thiophenecarboxylate (Compound No. 3366)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.84 (1H, s), 7.56 (1H, s) 7.14-7.05 (2H,m), 6.90-6.83 (1H, m), 2.14 (3H, s), 1.83-1.69 (1H, m), 0.79-0.68 (2H,m), 0.65-0.55 (2H, m). Appearance: amorphous.

EXAMPLE 579 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-thiophenecarboxylate (Compound No. 3372)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.42-8.40 (1H, m), 7.70-7.66 (1H, m),7.58 (1H, s), 7.47-7.41 (1H, m), 7.13-7.05 (2H, m), 6.88-6.82 (1H, m),2.15 (3H, s), 1.84-1.70 (1H, m), 0.80-0.68 (2H, m), 0.64-0.55 (2H, m).Appearance: paste state.

EXAMPLE 580 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methoxy-3-thiophenecarboxylate (Compound No. 3378)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.33 (1H, d, J=3.5 Hz), 7.59 (1H, s),7.09-7.06 (2H, m), 6.87-6.82 (1H, m), 6.38 (1H, d, J=3.5 Hz), 3.93 (3H,s), 2.16 (3H, s), 1.82-1.74 (1H, m), 0.75-0.56 (4H, m). Melting point (°C.): 146-149.

EXAMPLE 581 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-benzyl-3-tert-butyl-1H-pyrazole-5-carboxylate (Compound No. 3384)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.44 (1H, s), 7.21 (5H, s), 7.09-7.06(2H, m), 6.98 (1H, s), 6.85-6.80 (1H, m), 5.72 (2H, s), 2.08 (3H, s),1.76-1.64 (1H, m), 1.36 (9H, s), 0.75-0.64 (2H, m), 0.59-0.50 (2H, m).Appearance: paste state.

EXAMPLE 582 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-chloro-1,3-dimethyl-1H-pyrazole-4-carboxylate (Compound No. 3390)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.62 (1H, s), 7.09-7.07 (2H, m),6.87-6.82 (1H, m), 3.86 (3H, s), 2.52 (3H, s), 2.14 (3H, s), 1.84-1.77(1H, m), 0.75-0.67 (2H, m), 0.60-0.53 (2H, m). Appearance: paste state.

EXAMPLE 583 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylate (Compound No. 3396)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.53 (1H, s), 7.48-7.42 (2H, m),7.41-7.30 (2H, m), 7.08-7.06 (2H, m), 6.83-6.78 (1H, m), 2.89 (3H, s),2.02 (3H, s), 1.67-1.53 (1H, m), 0.68-0.50 (4H, m). Appearance:amorphous.

EXAMPLE 584 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methyl-1,2,3-thiadizaole-5-carboxylate (Compound No. 3402)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.15-7.05 (2H, m),6.91-6.84 (1H, m), 3.08 (3H, s), 2.14 (3H, s), 1.80-1.65 (1H, m),0.80-0.72 (2H, m), 0.64-0.53 (2H, m). Appearance: paste state.

EXAMPLE 585 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl6-methyl-2-pyridinecarboxylate (Compound No. 3408)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.12 (1H, d, J=7.7 Hz), 7.82 (1H, t,J=7.7 Hz), 7.55 (1H, s), 7.46 (1H, d, J=7.7 Hz), 7.12-7.02 (2H, m),6.85-6.76 (1H, m), 2.71 (3H, s), 2.15 (3H, s), 1.87-1.74 (1H, m),0.82-0.52 (4H, m). Appearance: caramel-like.

EXAMPLE 586 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5-butyl-2-pyridinecarboxylate (Compound No. 3414)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.67 (1H, br.s), 8.22 (1H, d, J=7.7 Hz),7.74 (1H, br.d, J=7.7 Hz), 7.53 (1H, s), 7.08-7.05 (2H, m), 6.83-6.78(1H, m), 2.75 (2H, t, J=7.7 Hz), 2.15 (3H, s), 1.84-1.59 (3H, m),1.48-1.32 (2H, m), 0.95 (3H, t, J=7.0 Hz), 0.75-0.54 (4H, m).Appearance: caramel-like.

EXAMPLE 587 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylnicotinate (Compound No. 3420)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.42-9.41 (1H, m), 8.91 (1H, dd, J=4.8,0.8 Hz), 8.50-8.44 (1H, m), 7.60 (1H, s), 7.56-7.49 (1H, m), 7.13-7.04(2H, m), 6.88-6.78 (1H, m), 2.15 (3H, s), 1.90-1.70 (1H, m), 0.81-0.70(2H, m), 0.63-0.55 (2H, m). Appearance: paste state.

EXAMPLE 588 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-chloronicotinate (Compound No. 3426)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.66 (1H, dd, J=4.8, 2.0 Hz), 8.45 (1H,dd, J=7.7, 2.0 Hz), 7.59 (1H, s), 7.45 (1H, dd, J=7.7, 4.8 Hz),7.14-7.06 (2H, m), 6.89-6.83 (1H, m), 2.15 (3H, s), 1.84-1.70 (1H, m),0.80-0.52 (4H, m). Appearance: caramel-like.

EXAMPLE 589 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-methylnicotinate (Compound No. 3432)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.74 (1H, dd, J=4.8, 1.5 Hz), 8,46 (1H,dd, J=7.7, 1.5 Hz), 7.58 (1H, s), 7.34 (1H, dd, J=7.7, 4.8 Hz),7.13-7.05 (2H, m), 6.89-6.83 (1H, m), 2.93 (3H, s), 2.15 (3H, s),1.83-1.67 (1H, m), 0.80-0.68 (2H, m), 0.65-0.55 (2H, m). Appearance:paste state.

EXAMPLE 590 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-phenoxynicotinate (Compound No. 3438)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.50 (1H, dd, J=7.8, 2.2 Hz), 8.39 (1H,dd, J=4.8, 2.2 Hz), 7.61 (1H, s), 7.46-7.38 (2H, m), 7.29-7.20 (1H, m),7.19-7.04 (5H, m), 6.86-6.81 (1H, m), 2.14 (3H, s), 1.85-1.72 (1H, m),1.36 (9H, s), 0.75-0.65 (2H, m), 0.58-0.52 (2H, m). Appearance: pastestate.

EXAMPLE 591 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-(methylsulfanyl)nicotinate (Compound No. 3444)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.70 (1H, dd, J=4.9, 1.8 Hz), 8.47 (1H,dd, J=7.7, 1.8 Hz), 7.63 (1H, s), 7.16 (1H, dd, J=7.7, 4.8 Hz) 7.12-7.05(2H, m), 6.89-6.82 (1H, m), 2.59 (3H, s), 2.16 (3H, s), 1.84-1.71 (1H,m), 0.80-0.70 (2H, m), 0.65-0.53 (2H, m). Appearance: paste state.

EXAMPLE 592 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-(allylsulfanyl)nicotinate (Compound No. 3450)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.67 (1H, dd, J=4.8, 1.8 Hz), 8.46 (1H,dd, J=8.2, 1.8 Hz), 7.62 (1H, s), 7.16 (1H, dd, J=8.2, 4.8 Hz),7.09-7.04 (2H, m), 6.89-6.82 (1H, m), 6.10-5.90 (1H, m), 5.33 (1H, dd,J=16.8, 1.6 Hz), 5.12 (1H, dd, J=11.0, 1.2 Hz), 3.91 (1H, dd, J=6.8, 1.2Hz), 2.15 (3H, s), 1.85-1.70 (1H, m), 0.78-0.71 (2H, m), 0.60-0.51 (2H,m). Appearance: paste state.

EXAMPLE 593 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-(phenylsulfanyl)nicotinate (Compound No. 3456)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.50 (1H, s), 8.47 (1H, d, J=2.6 Hz),7.65 (1H, s), 7.59-7.51 (2H, m), 7.48-7.41 (3H, m), 7.17-7.05 (3H, m),6.90-6.82 (1H, m), 2.18 (3H, s), 1.89-1.74 (1H, m), 0.82-0.70 (2H, m),0.65-0.54 (2H, m). Appearance: paste state.

EXAMPLE 594 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(trifluoromethyl)nicotinate (Compound No. 3462)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.42 (1H, s), 9.08 (1H, d, J=5.1 Hz),7.79 (1H, d, J=5.1 Hz), 7.57 (1H, s), 7.14-7.06 (2H, m), 6.90-6.84 (1H,m), 2.16 (3H, s), 1.84-1.72 (1H, m), 0.79-0.71 (2H, m), 0.63-0.55 (2H,m). Melting point (° C.): 92-93.

EXAMPLE 595 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl6-chloronicotinate (Compound No. 3468)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.19 (1H, d, J=2.0), 8.40 (1H, dd, J=8.4,2.6), 7.59 (1H, s), 7.54 (1H, d, J=8.4 Hz), 7.10-7.08 (1H, m), 7.07 (1H,s), 6.87-6.82 (1H, m), 2.14 (3H, s), 1.79-1.65 (1H, m), 0.79-0.70 (2H,m), 0.62-0.53 (2H, m). Appearance: paste state.

EXAMPLE 596 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,6-dichloronicotinate (Compound No. 3474)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.46 (1H, d, J=8.1 Hz), 7.67 (1H, s),7.52 (1H, d, J=8.1 Hz), 7.13-7.02 (2H, m), 6.90-6.75 (1H, m), 2.14 (3H,s), 1.85-1.68 (1H, m), 0.85-0.48 (4H, m). Appearance: amorphous.

EXAMPLE 597 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-chloro-6-methylnicotinate (Compound No. 3480)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.37 (1H, d, J=7.7 Hz), 7.58 (1H, s),7.27 (1H, d, J=7.7 Hz), 7.14-7.08 (2H, m), 6.89-6.80 (1H, m), 2.65 (3H,s), 2.15 (3H, s), 1.83-1.69 (1H, m), 0.80-0.70 (2H, m), 0.68-0.55 (2H,m). Appearance: paste state.

EXAMPLE 598 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl5,6-dichloronicotinate (Compound No. 3486)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.07 (1H, d, J=2.2 Hz), 8.50 (1H, d,J=2.2 Hz), 7.57 (1H, s), 7.10-7.07 (2H, m), 6.87-6.82 (1H, m), 2.13 (3H,s), 1.80-1.65 (1H, m), 0.75-0.70 (2H, m), 0.58-0.55 (2H, m). Appearance:paste state.

EXAMPLE 599 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2-chloroisonicotinate (Compound No. 3492)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.68 (1H, d, J=5.0 Hz), 8.05 (1H, s),7.95-7.92 (1H, m), 7.57 (1H, s), 7.10-7.07 (2H, m), 6.87-6.83 (1H, m),2.14 (3H, s), 1.77-1.68 (1H, m), 0.75-0.71 (2H, m), 0.58-0.56 (2H, m).Appearance: paste state.

EXAMPLE 600 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-benzofuran-2-carboxylate (Compound No. 3498).

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.86-7.75 (2H, m), 7.68-7.51 (3H, m),7.38 (1H, dd, J=7.7, 7.0 Hz), 7.12-7.05 (2H, m), 6.89-6.80 (1H, m), 2.17(3H, s), 1.86-1.73 (1H, m), 0.80-0.68 (2H, m), 0.64-0.55 (2H, m).Appearance: amorphous.

EXAMPLE 601 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-benzothiophene-2-carboxylate (Compound No. 3504)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.34 (1H, s), 7.94 (2H, m), 7.64 (1H, s),7.59-7.42 (2H, m), 7.09-7.07 (2H, m), 6.87-6.83 (1H, m), 2.18 (3H, s),1.88-1.72 (1H, m), 0.77-0.71 (2H, m), 0.61-0.53 (2H, m). Melting point(° C.): 105-107.

EXAMPLE 602 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1,3-benzothiazole-6-carboxylate (Compound No. 3510)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 9.24 (1H, s), 8.89 (1H, d, J=1.4 Hz),8.36 (1H, dd, J=8.4, 1.4 Hz), 8.28 (1H, d, J=8.4 Hz), 7.65 (1H, s),7.09-7.06 (2H, m), 6.87-6.82 (1H, m), 2.17 (3H, s), 1.86-1.73 (1H, m),0.78-0.72 (2H, m), 0.63-0.55 (2H, m). Appearance: amorphous.

EXAMPLE 603 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1,3-benzodioxole-5-carboxylate (Compound No. 3516)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.85 (1H, dd, J=8.4, 1.8 Hz), 7.60-7.59(2H, m), 7.09-7.06 (2H, m), 6.93 (1H, d, J=8.0 Hz), 6.86-6.82 (1H, m),6.10 (2H, s), 2.15 (3H, s), 1.86-1.74 (1H, m), 0.79-0.70 (2H, m),0.62-0.53 (2H, m). Appearance: paste state.

EXAMPLE 604 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-isoquinolinecarboxylate (Compound No. 3522)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.45 (1H, d, J=8.1 Hz), 7.78-7.70 (2H,m), 7.61-7.53 (2H, m), 7.16 (1H, d, J=7.7 Hz), 7.12-7.05 (2H, m),6.90-6.83 (1H, m), 6.66 (1H, d, J=7.3 Hz), 2.15 (3H, s), 1.81-1.66 (1H,m), 0.79-0.67 (2H, m), 0.63-0.53 (2H, m). Appearance: amorphous.

EXAMPLE 605 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyltert-butyl(methyl)carbamate (Compound No. 3528)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.51 (1H, s), 7.15-7.03 (2H, m),6.90-6.80 (1H, m), 3.11 (3H, s), 2.14 (3H, s), 1.85-1.70 (1H, m), 1.47(9H, S), 0.80-0.50 (4H, m) Melting point (° C.): 113-115.

EXAMPLE 606 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldibutylcarbamate (Compound No. 3534)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.15-7.03 (2H, m),6.90-6.78 (1H, m), 3.50-3.26 (4H, m), 2.13 (3H, s), 1.87-1.50 (5H, m),1.50-1.15 (4H, m), 1.10-0.85 (6H, m), 0.80-0.54 (4H, m). Appearance:caramel-like.

EXAMPLE 607 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbenzyl(methyl)carbamate (Compound No. 3540)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (0.5H, s), 7.57 (0.5H, s), 7.40-7.20(5H, m), 7.15-7.03 (2H, m), 6.92-6.80 (1H, m), 4.68 (1H, s), 4.57 (1H,s), 3.08 (1.5H, s), 3.02 (1.5H, s), 2.15 (1.5H, s), 2.13 (1.5H, s),1.85-1.65 (1H, m), 0.80-0.45 (4H, m). Appearance: caramel-like.

EXAMPLE 608 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylcyanomethyl(methyl)carbamate (Compound No. 3546)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (0.4H, s), 7.56 (0.6H, s), 7.15-7.04(2H, m), 6.90-6.80 (1H, m), 4.42 (0.8H, s), 4.36 (1.2H, s), 3.30 (1.8H,s), 3.19 (1.2H, s), 2.14 (3H, s), 1.85-1.62 (1H, m), 0.80-0.53 (4H, m).Appearance: caramel-like.

EXAMPLE 609 EthylN-({[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]oxy}carbonyl)-N-methylglycinate(Compound No. 3552)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.61 (0.5H, s), 7.60 (0.5H, s), 7.15-7.02(2H, m), 6.90-6.80 (1H, m), 4.28-4.11 (4H, m), 3.23 (1.5H, s), 3.13(1.5H, s), 2.15 (1.5H, s), 2.13 (1.5H, s), 1.85-1.65 (1H, m), 1.31-1.18(3H, m), 0.80-0.50 (4H, m) Appearance: caramel-like.

EXAMPLE 610 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethyl(2-pyridinyl)carbamate (Compound No. 3558)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.35-8.25 (1H, m), 7.70-7.55 (1H, m),7.05-6.90 (5H, m), 6.85-6.74 (1H, m), 3.56 (3H, s), 2.03 (3H, s),1.72-1.55 (1H, m), 0.75-0.45 (4H, m). Melting point (° C.): 140-147.

EXAMPLE 611 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-piperidinecarboxylate (Compound No. 3636)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56 (1H, s), 7.15-7.03 (2H, m),6.90-6.80 (1H, m), 3.70-3.60 (2H, m), 3.60-3.45 (2H, m), 2.15 (3H, s),1.86-1.70 (1H, m), 1.70-1.50 (6H, m), 0.80-0.53 (4H, m). Appearance:caramel-like.

EXAMPLE 612 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbis(2-chloroethyl)carbamate (Compound No. 3570)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.58 (1H, s), 7.15-7.05 (2H, m),6.92-6.82 (1H, m), 3.98-3.70 (8H, m), 2.13 (3H, s), 1.82-1.65 (1H, m),0.80-0.50 (4H, m). Melting point (° C.): 166-167.

EXAMPLE 613 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldiallylcarbamate (Compound No. 3576)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.56 (1H, s), 7.12-7.04 (2H, m),6.88-6.80 (1H, m), 6.00-5.70 (2H, m), 5.30-5.15 (4H, m), 4.10-3.93 (4H,m), 2.13 (3H, s), 1.85-1.68 (1H, m), 0.80-0.52 (4H, m). Appearance:caramel-like.

EXAMPLE 614 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbis(cyanomethyl)carbamate (Compound No. 3582)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.18-7.05 (2H, m),6.90-6.80 (1H, m), 4.54 (2H, s), 4.48 (2H, s), 2.13 (3H, s), 1.80-1.65(1H, m), 0.80-0.50 (4H, m). Appearance: caramel-like.

EXAMPLE 615 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbis(2-cyanoethyl)carbamate (Compound No. 3588)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.61 (1H, s), 7.18-7.05 (2H, m),6.92-6.82 (1H, m), 3.91 (2H, t, J=6.6 Hz), 3.77 (2H, t, J=6.2 Hz), 2.85(2H, t, J=6.6 Hz), 2.78 (2H, t, J=6.2 Hz), 2.13 (3H, s), 1.80-1.63 (1H,m), 0.82-0.53 (4H, m). Melting point (° C.): 159-161.

EXAMPLE 616 EthylN-({[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]oxy}carbonyl)-N-(2-ethoxy-2-oxoethyl)glycinate(Compound No. 3594)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.65 (1H, s), 7.13-7.03 (2H, m),6.90-6.80 (1H, m), 4.33-4.05 (8H, m), 2.12 (3H, s), 1.83-1.65 (1H, m),1.28 (3H, t, J=7.3 Hz), 1.19 (3H, t, J=7.3 Hz), 0.80-0.50 (4H, m).Appearance: caramel-like.

EXAMPLE 617 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbis(2-methoxyethyl)carbamate (Compound No. 3600)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.15-7.05 (2H, m),6.90-6.80 (1H, m), 3.80-3.50 (8H, m), 3.32 (6H, s), 2.15 (3H, s),1.86-1.69 (1H, m), 0.80-0.52 (4H, m). Appearance: caramel-like.

EXAMPLE 618 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbis(2-ethoxyethyl)carbamate (Compound No. 3606)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.57 (1H, s), 7.15-7.03 (2H, m),6.90-6.80 (1H, m), 3.78-3.55 (8H, m), 3.46 (4H, q, J=6.9 Hz), 2.14 (3H,s), 1.87-1.65 (1H, m), 1.15 (3H, t, J=6.9 Hz), 1.14 (3H, t, J=6.9 Hz),0.80-0.53 (4H, m). Appearance: caramel-like.

EXAMPLE 619 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-azetizinecarboxylate (Compound No. 3612)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.53 (1H, s), 7.13-7.02 (2H, m),6.90-6.78 (1H, m), 4.38-4.05 (4H, m), 2.45-2.29 (2H, m), 2.15 (3H, s),1.85-1.67 (1H, m), 0.80-0.50 (4H, m). Melting point (° C.): 134-136.

EXAMPLE 620 1-[6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]2-methyl 1,2-pyrrolidinedicarboxylate (Compound No. 3618)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.65 (0.5H, s), 7.62 (0.5H, s), 7.15-7.02(2H, m), 6.90-6.78 (1H, m), 4.63-4.57 (0.5H, m), 4.51-4.44 (0.5H, m),3.91-3.55 (2H, m), 3.75 (1.5H, s), 3.65 (1.5H, s), 2.50-1.90 (4H, m),2.15 (1.5H, s), 2.13 (1.5H, s), 1.90-1.69 (1H, m), 0.80-0.50 (4H, m).Appearance: caramel-like.

EXAMPLE 621 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl3-hydroxy-1-pyrrolidinecarboxylate (Compound No. 3624)

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.60 (1H, s), 7.13-7.03 (2H, m),6.90-6.80 (1H, m), 4.65-4.52 (1H, m), 3.85-3.55 (4H, m), 2.14 (3H, s),2.13-2.00 (2H, m), 1.87-1.70 (2H, m), 0.80-0.50 (4H, m). Appearance:caramel-like.

EXAMPLE 6226-Chloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 1126) (1) 2,3,5-Trimethylphenyl acetate

In dichloromethane (150 mL) was dissolved 15.09 g (0.1108 mol) of2,3,5-trimethylphenol, and 17.82 mL (0.2204 mol) of pyridine, then 20.78mL (0.2202 mol) of acetic anhydride were added to the solution, and themixture was stirred at room temperature overnight. The reaction mixturewas poured into water, and extracted with dichloro-methane. The organiclayer was successively washed with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (Wako gel C-100,hexane:ethyl acetate, gradient) to obtain 20.08 g (0.1127 mol, Yield:quantitative) of 2,3,5-trimethylphenyl acetate.

(2) 1-(2-Hydroxy-3,4,6-trimethylphenyl)ethanone

To 13.83 g (77.60 mmol) of 2,3,5-trimethylphenyl acetate obtained in (1)was added 20.69 g (155.2 mmol) of aluminum chloride little by little inan ice bath with stirring. The mixture was stirred while heating to 100°C. overnight. After cooling, the reaction mixture was added to ice waterlittle by little. The mixture was extracted with dichloromethane, theorganic layers were combined, washed with water, and dried overanhydrous magnesium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (Wako gel C-100,hexane:ethyl acetate, gradient) to obtain 12.75 g (71.55 mmol, Yield:92.20%) of 1-(2-hydroxy-3,4,6-trimethylphenyl)ethanone.

(3) 1-(2-Methoxy-3,4,6-trimethylphenyl)ethanone

In acetone (100 mL) was dissolved 8.00 g (44.9 mmol) of1-(2-hydroxy-3,4,6-trimethylphenyl)ethanone obtained in (2), to themixture were added 18.6 g (135 mmol) of potassium carbonate, and then,8.40 mL (135 mmol) of methyl iodide, and the resulting mixture wasrefluxed for 27 hours and 30 minutes. Moreover, 18.6 g (135 mmol) ofpotassium carbonate, and 8.40 mL (135 mmol) of methyl iodide wereadditionally added to the mixture, and the resulting mixture wasrefluxed for 6 hours. The reaction mixture was concentrated underreduced pressure, water (100 mL) was added to the residue, and themixture was extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous sodium sulfate. The solvent was removed, and the residue waspurified by silica gel column chromatography (Daisogel 1001W,hexane:ethyl acetate, gradient) to obtain 8.04 g (41.9 mmol, Yield:93.3%) of 1-(2-methoxy-3,4,6-trimethylphenyl)ethanone.

(4) 1-(2-Methoxy-3,4,6-trimethylphenyl)ethanol

In methanol (100 mL) was dissolved 5.01 g (26.1 mmol) of1-(2-methoxy-3,4,6-trimethylphenyl)ethanone obtained in (3), and in anice bath, 1.00 g (26.5 mmol) of sodium borohydride was added to thesolution and the mixture was stirred in an ice bath for 2 hours and 30minutes. The reaction mixture was poured into 400 mL of ice water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed to obtain 4.35g (22.4 mmol, Yield:85.8%) of 1-(2-methoxy-3,4,6-trimethylphenyl)ethanol.

(5) 2-(1-Chloroethyl)-3-methoxy-1,4,5-trimethylbenzene

To 0.652 g (3.36 mmol) of 1-(2-methoxy-3,4,6-trimethylphenyl)ethanolobtained in (4) was added dropwise with stirring 0.150 mL (1.72 mmol) ofoxalyl chloride, and the mixture was stirred at 100° C. for 2 hours.Then, dichloromethane (1 mL) and triethylamine (3 mL) were added to thereaction mixture, and the resulting mixture was stirred at 100° C. for 3hours. The reaction mixture was poured into 60 ml of ice water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed to obtain 0.620 g (2.91 mmol, Yield:86.6%) of 2-(1-chloroethyl)-3-methoxy-1,4,5-trimethylbenzene.

(6) 3-Methoxy-1,2,5-trimethyl-4-vinylbenzene

In N,N-dimethylformamide (DMF, 6 mL) was dissolved 0.620 g (2.91 mmol)of 2-(1-chloroethyl)-3-methoxy-1,4,5-trimethylbenzene obtained in (5),and 1.20 g (8.70 mmol) of potassium carbonate was added to the solutionand the resulting mixture was refluxed for 9 hours. The reaction mixturewas poured into 50 ml of ice water, and extracted with hexane. Theorganic layers were combined, washed successively with water and brine,and dried over anhydrous sodium sulfate. The solvent was removed, andthe residue was purified by silica gel column chromatography (Daisogel1001W, hexane:ethyl acetate, gradient) to obtain 0.360 g (2.05 mmol,Yield: 70.4%) of 3-methoxy-1,2,5-trimethyl-4-vinylbenzene.

(7) 2-Cyclopropyl-3-methoxy-1,4,5-trimethylbenzene

To dry dichloromethane (5 mL) was added 3.07 mL (3.04 mmol) of diethylzinc (0.99 mol/L hexane solution), a dichloromethane (2.5 mL) solutioncontaining 0.23 mL (3.0 mmol) of trifluoroacetic acid was graduallyadded dropwise with stirring in an ice bath. After completion of thedropwise addition, the mixture was stirred in an ice bath for 30minutes, and 0.24 mL (3.0 mmol) of diiodomethane was added dropwise tothe mixture. Then, a dichloromethane (3 mL) solution containing 0.268 g(1.52 mmol) of 3-methoxy-1,2,5-trimethyl-4-vinylbenzene obtained in (6)was added dropwise, and the mixture was stirred in an ice bath for 1hour. The reaction mixture was poured into water, made acidic withdiluted hydrochloric acid, and then, extracted with dichloromethane. Theorganic layers were combined, washed with water, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05717, 2 plates were used, developed byhexane:ethyl acetate=25:1) to obtain 0.212 g (1.12 mmol, Yield: 73.7%)of 2-cyclopropyl-3-methoxy-1,4,5-trimethylbenzene.

(8) 2-Cyclopropyl-3,5,6-trimethylphenol

Under nitrogen atmosphere, in dry N,N-dimethylformamide (5 mL) wassuspended 134 mg (3.35 mmol) of 60% sodium hydride, and 0.26 mL (3.5mmol) of ethanethiol was gradually added dropwise to the suspension.After stirring for 30 minutes, a dry N,N-dimethylformamide (5 mL)solution containing 0.212 g (1.12 mmol) of2-cyclopropyl-3-methoxy-1,4,5-trimethylbenzene obtained in (7) was addeddropwise to the mixture, and the resulting mixture was stirred at 160°C. for 5 hours. After allowing to stand for cooling, the reactionmixture was poured into water, made acidic by adding dilutedhydrochloric acid, and extracted with ethyl acetate. The organic layerswere combined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 3 plates were used, developed byethyl acetate:hexane=25:1) to obtain 179 mg (1.02 mmol, Yield: 91.1%) of2-cyclopropyl-3,5,6-trimethylphenol.

(9) Mixture of6-chloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine 1-oxide(Step B-2)

179 mg (1.02 mmol) of 2-cyclopropyl-3,5,6-trimethylphenol, 1,4-dioxane(5 mL) and dimethylsulfoxide (5 mL) were mixed, 125 mg (1.12 mmol) ofpotassium tert-butoxide was added to the mixture, and the resultingmixture was stirred for 10 minutes. To the mixture was added 167 mg(1.01 mmol) of 3,6-dichloropyridazine 1-oxide, and the mixture wasallowed to stand at room temperature for 3 days. The reaction mixturewas poured into water, and extracted with ethyl acetate. The organiclayers were combined, washed successively with water and brine, anddried over anhydrous magnesium sulfate. The solvent was distilled offand the obtained residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05717, 2 plates were used,developed by hexane:ethyl acetate=2:1) to obtain 263 mg of a mixture of6-chloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine 1-oxide.

(10) 4,6-Dichloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine(Step B-3)

263 mg of a mixture of6-chloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine 1-oxideobtained in (9) and 3.0 mL (32 mmol) of phosphorus oxychloride weremixed, and the mixture was stirred at room temperature overnight.Dichloromethane and water were added to the reaction mixture, and afterstirring, the mixture was extracted with dichloromethane. The organiclayers were combined, washed with water, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the obtainedresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05717, 2 plates were used, developed by hexane:ethylacetate=2:1) to obtain 198 mg (0.613 mmol, Yield from3,6-dichloropyridazine 1-oxide: 60.7%) of4,6-dichloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine. Also,43.8 mg (0.144 mmol, Yield from 3,6-dichloropyridazine 1-oxide: 14.2%)of 3-chloro-6-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine 1-oxidewas obtained.

(11) 6-Chloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 1126, Step A-3 and A-4)

In dimethylsulfoxide (10 mL) was dissolved 198 mg (0.613 mmol) of4,6-dichloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)pyridazine obtainedin (10), 251 mg (3.06 mmol) of sodium acetate was added to the solutionand the mixture was stirred at 120° C. for 4 hours. The reaction mixturewas cooled, poured into water, and made acidic with diluted hydrochloricacid. The mixture was extracted with ethyl acetate, the organic layerswere combined, washed with water, and dried over anhydrous magnesiumsulfate. The solvent was distilled off and the obtained residue waspurified by preparative thin-layer chromatography (available from MERCKCO., 1.05717, 2 plates were used, developed by hexane:ethyl acetate=1:2)to obtain 116 mg (0.380 mmol, Yield: 62.0%) of6-chloro-3-(2-cyclopropyl-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 1126).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.67 (1H, s), 6.62 (1H, s), 2.22 (3H, s),2.16 (3H, s), 2.05 (3H, s), 1.85-1.65 (1H, m), 0.75-0.62 (2H, m),0.60-0.45 (2H, m). Melting point (° C.): 212-219.

EXAMPLE 623 6-Chloro-3-(2-methoxy-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 1128) (1) 1-[2-(Benzyloxy)-3,4,6-trimethylphenyl]ethanone

In N,N-dimethylformamide (8 mL) was dissolved 2.00 g (11.2 mmol) of1-(2-hydroxy-3,4,6-trimethylphenyl)ethanone obtained in Example 622 (2).To the solution was added in an ice bath 0.488 g (11.2 mmol) of 60%sodium hydride, and after stirring in an ice bath for 10 minutes, 1.92 g(11.2 mmol) of benzyl bromide was gradually added dropwise and themixture was stirred at room temperature overnight. The reaction mixturewas poured into ice water, and extracted with ethyl acetate. The organiclayer was successively washed with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel column chromatography (Wako gelC-100, hexane-ethyl acetate, gradient) to obtain 2.36 g (8.81 mmol,Yield: 78.7%) of 1-[2-(benzyloxy)-3,4,6-trimethylphenyl]ethanone.

(2) 2-(Benzyloxy)-3,4,6-trimethylphenyl acetate

In dichloromethane (3 mL) was dissolved 500 mg (1.87 mmol) of1-[2-(benzyloxy)-3,4,6-trimethylphenyl]ethanone obtained in (1), adichloromethane (6 mL) solution containing 921 mg (purity 70-75%,3.73-3.99 mmol) of m-chloroper-benzoic acid was added to the solution,and the resulting mixture was stirred at room temperature for 2 days.The reaction mixture was poured into a saturated aqueous sodium sulfitesolution, and extracted with ethyl acetate. The organic layer was washedwith a saturated aqueous sodium hydrogen carbonate solution, and driedover anhydrous sodium sulfate. The solvent was removed to obtain 560 mgof 2-(benzyloxy)-3,4,6-trimethylphenyl acetate.

(3) 2-(Benzyloxy)-3,4,6-trimethylphenol

In ethanol (15 mL) was dissolved 560 mg of2-(benzyloxy)-3,4,6-trimethylphenyl acetate obtained in (2), 2N aqueoussodium hydroxide solution was added to the solution and the resultingmixture was stirred at room temperature overnight and at 60° C. for 4hours. The reaction mixture was cooled up to room temperature, andpoured into water. To the mixture was added 1N hydrochloric acid to makethe mixture acidic, and the mixture was extracted with ethyl acetate.The organic layers were combined, washed successively with water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate, gradient) toobtain 290 mg (1.20 mmol, Yield from1-[2-(benzyloxy)-3,4,6-trimethylphenyl]ethanone: 64.2%) of2-(benzyloxy)-3,4,6-trimethylphenol.

(4) 3-(Benzyloxy)-2-methoxy-1,4,5-trimethylbenzene

In acetone (3 mL) was dissolved 290 mg (1.20 mmol) of2-(benzyloxy)-3,4,6-trimethylphenol obtained in (3), 350 mg (2.54 mmol)of potassium carbonate was added to the solution, and the mixture wasstirred at room temperature for 15 minutes. Then, 0.180 mL (2.89 mmol)of methyl iodide was added to the mixture, and the resulting mixture wasstirred at room temperature overnight. The reaction mixture was pouredinto water, and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 3 plates were used, developed byethyl acetate:hexane=10:1) to obtain 196 mg (0.766 mmol, Yield: 63.8%)of 3-(benzyloxy)-2-methoxy-1,4,5-trimethylbenzene.

(5) 2-Methoxy-3,5,6-trimethylphenol

In methanol (3 mL) was dissolved 180 mg (0.703 mmol) of3-(benzyloxy)-2-methoxy-1,4,5-trimethylbenzene obtained in (4), 0.10 gof 5% palladium-carbon was added to the solution, and the mixture wasstirred under hydrogen atmosphere (1 atm) for 4 hours. The reactionmixture was filtered through Celite, and the filtrate was concentrated.90.7 mg (0.546 mmol, Yield: 77.7%) of 2-methoxy-3,5,6-trimethylphenolwas obtained.

(6) Mixture of 6-chloro-3-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine1-oxide and 3-chloro-6-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine1-oxide (Step B-2)

90.0 mg (0.542 mmol) of 2-methoxy-3,5,6-trimethylphenol obtained in (5),1,4-dioxane (1.5 mL) and dimethylsulfoxide (1.5 mL) were mixed, 73.5 mg(0.656 mmol) of potassium tert-butoxide was added to the mixture, andthe resulting mixture was stirred in an ice bath for 15 minutes. To themixture was added 93.2 mg (0.565 mmol) of 3,6-dichloropyridazine1-oxide, and the resulting mixture was stirred at room temperature for 3hours. The reaction mixture was poured into water, and extracted withethyl acetate. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by hexane:ethyl acetate=2:1) toobtain 140 mg of a mixture of6-chloro-3-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine 1-oxide.

(7) 4,6-Dichloro-3-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine (StepB-3)

140 mg of a mixture of6-chloro-3-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine 1-oxide and3-chloro-6-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine 1-oxide obtainedin (6) and 0.25 mL (2.7 mmol) of phosphorus oxychloride were mixed, andthe mixture was stirred at room temperature overnight. The reactionmixture was poured into water, and extracted with dichloromethane. Theorganic layers were combined, washed successively with water and brine,and dried over anhydrous magnesium sulfate. The solvent was distilledoff and the obtained residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05744, 3 plates were used,developed by hexane:ethyl acetate=2:1) to obtain 111 mg (0.355 mmol,Yield from 3,6-dichioropyridazine 1-oxide: 62.8%) of4,6-dichloro-3-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine. Also, 38.3mg (0.130 mmol, Yield from 3,6-dichloropyridazine 1-oxide: 23.0%) of3-chloro-6-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine 1-oxide wasobtained.

(8) 6-Chloro-3-(2-methoxy-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 1128, Step B-4)

To a dimethylsulfoxide (10 mL) solution containing 111 mg (0.355 mmol)of 4,6-dichloro-3-(2-methoxy-3,5,6-trimethylphenoxy)pyridazine obtainedin (7) was added 0.3 mL (0.6 mmol) of 2 mol/L aqueous sodium hydroxidesolution, and the mixture was stirred at room temperature for 2 hoursand 30 minutes. The reaction mixture was poured into ice-cooled 1 mol/Laqueous sodium hydroxide solution, and extracted with ethyl acetate. Theaqueous layer was separated, made acidic by adding conc. hydrochloricacid in an ice bath, and extracted with ethyl acetate. The organiclayers were combined, washed successively with water and brine, anddried over magnesium sulfate. The solvent was removed, and the obtainedresidue was washed with ether to obtain 38.9 mg (0.132 mmol, Yield:37.2%) of 6-chloro-3-(2-methoxy-3,5,6-trimethylphenoxy)-4-pyridazinol(Compound No. 1128).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 6.73 (1H, s), 6.67 (1H, s), 3.69 (3H, s),2.29 (3H, s), 2.15 (3H, s),-2.09 (3H, s). Melting point (° C.): 209-210.

EXAMPLE 624 6-Chloro-3-[2-(1-isopropylvinyl)phenoxy]-4-pyridazinol(Compound No. 2529) and6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-4-pyridazinol (CompoundNo. 2542) (1) 1-[2-(Methoxymethoxy)phenyl]ethanone

In N,N-dimethylformamide (25 mL) was dissolved 3.39 g (24.9 mmol) ofcommercially available 1-(2-hydroxyphenyl)-ethanone, 1.52 g (38.0 mmol)of 60% sodium hydride was added to the solution in an ice bath, and theresulting mixture was stirred in an ice bath for 20 minutes. To themixture was gradually added dropwise 3.00 mL (39.5 mmol) ofchloro(methoxy)methane, and the resulting mixture was stirred at roomtemperature overnight. The reaction mixture was poured into water, andextracted with ethyl acetate. The organic layer was successively washedwith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was removed, and the obtained residue was purified by silica gelcolumn chromatography (Wako gel C-100, hexane-ethyl acetate, gradient)to obtain 4.33 g (24.1 mmol, Yield: 96.8%) of1-[2-(methoxymethoxy)phenyl]ethanone.

(2) 2-[2-(Methoxymethoxy)phenyl]-3-methyl-2-butanol

In dry tetrahydrofuran (3 mL) was dissolved 1.00 g (5.56 mmol) of1-[2-(methoxymethoxy)phenyl]ethanone obtained in (1), and under nitrogenatmosphere and ice-cooling, 2.8 mL (5.6 mmol) of a tetrahydrofuransolution containing 2 mol/L isopropylmagnesium bromide was addeddropwise. After completion of dropwise addition, the reaction mixturewas stirred at room temperature for 1 hour and 30 minutes. The reactionmixture was poured into water, made acidic with diluted hydrochloricacid, and then, extracted with ether. The organic layers were combined,washed successively with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was removed, and the obtained residue waspurified by silica gel column chromatography (Wako gel C-100,hexane-ethyl acetate, gradient) to obtain 0.522 g (2.33 mmol, Yield:41.9%) of 2-[2-(methoxymethoxy)phenyl]-3-methyl-2-butanol.

(3) Mixture containing6-chloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine 1-oxide and6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]pyridazine 1-oxide, etc.

In dichloromethane (3 mL) was dissolved 0.522 g (2.33 mmol) of2-[2-(methoxymethoxy)phenyl]-3-methyl-2-butanol obtained in (2), and inan ice bath, 0.50 mL (3.6 mmol) of triethylamine, then, 0.25 mL (3.2mmol) of methanesulfonyl chloride were added to the solution, and theresulting mixture was stirred at room temperature overnight. Thereaction mixture was poured into water, and extracted withdichloromethane. The organic layer was successively washed with waterand brine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the residue was purified by silica gel columnchromatography (Wako gel C-100, hexane:ethyl acetate, gradient) toobtain 186 mg of a crude product containing2-(1,2-dimethyl-1-propenyl)phenol, etc. 132 mg of the crude product wasmixed with 1,4-dioxane (2 mL) and dimethylsulfoxide (2 mL), and 100 mg(0.893 mmol) of potassium tert-butoxide was added to the mixture. Then,to the mixture was added 119 mg (0.721 mmol) of 3,6-dichloropyridazine1-oxide, and the resulting mixture was stirred at room temperature for 5hours. The reaction mixture was poured into water, and extracted withethyl acetate. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was removed, and the obtained residue was purified by silica gelcolumn chromatography (Wako gel C-100, hexane:ethyl acetate, gradient)to obtain 220 mg of a mixture containing6-chloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine 1-oxide and6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]pyridazine 1-oxide, etc.

(4) 4,6-Dichloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine and4,6-dichloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-pyridazine (StepB-3)

In chloroform (0.4 mL) was dissolved 200 mg of a mixture containing6-chloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine 1-oxide and6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]pyridazine 1-oxide, etc.obtained in (3), 0.40 mL (4.3 mmol) of phosphorus oxychloride was mixedwith the mixture and the resulting mixture was stirred at 70° C. for 2hours. The reaction mixture was poured into water, and extracted withdichloromethane. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by hexane:acetone =20:1 threetimes) to obtain 23 mg of4,6-dichloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine (purity 86%,containing 14% of4,6-dichloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]pyridazine), and 50mg of 4,6-dichloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]pyridazine(purity 81%, containing 19% of4,6-dichloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine).

(5) 6-Chloro-3-[2-(1-isopropylvinyl)phenoxy]-4-pyridazinol (Compound No.2529, Step A-3 and A-4)

In dimethylsulfoxide (1 mL) was dissolved 23 mg of4,6-dichloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine (purity 86%,containing 14% of4,6-dichloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]pyridazine) obtainedin (4), 80 mg (0.98 mmol) of sodium acetate was added to the solutionand the mixture was stirred at 60° C. for 9 hours. The reaction mixturewas cooled, poured into water, and made acidic with diluted hydrochloricacid. The mixture was extracted with ethyl acetate, the organic layerswere combined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 2 plates were used, developed byhexane:ethyl acetate=1:1) to obtain 4.5 mg of6-chloro-3-[2-(1-isopropylvinyl)phenoxy]-4-pyridazinol (Compound No.2529, purity 91%, containing 9%6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-4-pyridazinol). Also,11.0 mg of 6-chloro-3-[2-(1-isopropylvinyl)phenoxy]-4-pyridazinol(containing 23%6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-4-pyridazinol) with apurity of 77% was obtained.

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.40-7.05 (4H, m), 6.59 (1H, s), 5.90(1H, s), 5.04 (1H, s), 2.71 (1H, septet, J=6.9 Hz), 0.98 (6H, d, J=6.9Hz). Appearance: amorphous.

(6) 6-Chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-4-pyridazinol(Compound No. 2542, Step A-3 and A-4)

In dimethylsulfoxide (2 mL) was dissolved 50 mg of4,6-dichloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-pyridazine (purity81%, containing 19% of4,6-dichloro-3-[2-(1-isopropylvinyl)phenoxy]pyridazine) obtained in (4),68 mg (0.83 mmol) of sodium acetate was added to the solution and theresulting mixture was stirred at 50° C. for 11 hours. The reactionmixture was cooled, poured into water, and made acidic with dilutedhydrochloric acid. The mixture was extracted with ethyl acetate, theorganic layers were combined, washed successively with water and brine,and dried over anhydrous magnesium sulfate. The solvent was distilledoff and the obtained residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05744, 2 plates were used,developed by hexane:ethyl acetate=2:1) to obtain 40.2 mg of6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-4-pyridazinol (CompoundNo. 2542, purity 86%, containing 14% of6-chloro-3-[2-(1-isopropylvinyl)phenoxy]-4-pyridazinol). Also, 3.7 mg of6-chloro-3-[2-(1,2-dimethyl-1-propenyl)phenoxy]-4-pyridazinol(containing 27% of6-chloro-3-[2-(1-isopropylvinyl)phenoxy]-4-pyridazinol) with a purity of73% was obtained.

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.38-7.05 (4H, m), 6.59 (1H, s), 1.78(3H, s), 1.62 (3H, s), 1.46 (3H, s). Appearance: amorphous.

EXAMPLE 625 6-Chloro-3-[2-(2-methyl-1-propenyl)phenoxy]-4-pyridazinol(Compound No. 2540) (1) 1-(2-Methoxyphenyl)-2-methyl-1-propanol

Dry tetrahydrofuran (3 mL) was added to 1.01 g (7.43 mmol) ofcommercially available 2-methoxybenzaldehyde under nitrogen atmosphere,and the mixture was ice-cooled. To the mixture was added dropwise a 3.8mL (7.6 mmol) of tetrahydrofuran solution containing 2 mol/Lisopropyl-magnesium bromide. After completion of dropwise addition, thereaction mixture was stirred in an ice bath for 1 hour. The reactionmixture was poured into water, made acidic with diluted hydrochloricacid, and then, extracted with ether. The organic layers were combined,washed successively with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was removed, and the obtained residue waspurified by silica gel column chromatography (Wako gel C-100,hexane-ethyl acetate, gradient) to obtain 1.00 g (5.56 mmol, Yield:74.8%) of 1-(2-methoxyphenyl)-2-methyl-1-propanol.

(2) 1-(l-Chloro-2-methylpropyl)-2-methoxybenzene

In dichloromethane (3 mL) was dissolved 630 mg (3.50 mmol) of1-(2-methoxyphenyl)-2-methyl-1-propanol obtained in (1), and then, 0.70mL (5.0 mmol) of triethylamine, then 0.35 mL (4.5 mmol) ofmethanesulfonyl chloride were added to the solution, and the resultingmixture was stirred for 1 hour. The reaction mixture was poured intowater, and extracted with dichloromethane. The organic layer wassuccessively washed with water and brine, and dried over anhydrousmagnesium sulfate. The solvent was removed to obtain 720 mg of1-(1-chloro-2-methylpropyl)-2-methoxybenzene.

(3) 1-Methoxy-2-(2-methyl-1-propenyl)benzene

In dry N,N-dimethylformamide (8 mL) was dissolved 410 mg of1-(1-chloro-2-methylpropyl)-2-methoxybenzene obtained in (2), and to thesolution was added 395 mg (3.52 mmol) of potassium tert-butoxide in anice bath. The reaction mixture was refluxed for 2 hours, then cooled toroom temperature, and poured into water. The mixture was extracted withhexane, the obtained organic layers were combined, washed successivelywith water and brine. The organic layer was dried over anhydrousmagnesium sulfate, and the solvent was removed to obtain 460 mg of1-methoxy-2-(2-methyl-1-propenyl)benzene.

(4) 2-(2-Methyl-1-propenyl)phenol

Under nitrogen atmosphere, in dry N,N-dimethylformamide (3 mL) wassuspended 60.0 mg (1.50 mmol) of 60% sodium hydride, and to thesuspension was gradually added dropwise 0.11 mL (1.5 mmol) ofethanethiol in an ice bath. After stirring for 10 minutes, a dryN,N-dimethylformamide (0.5 mL) solution containing 200 mg of1-methoxy-2-(2-methyl-1-propenyl)benzene obtained in (3) was addeddropwise to the mixture, and the resulting mixture was refluxed for 2hours and 30 minutes. After allowing to stand for cooling, the reactionmixture was poured into water, made acidic by adding dilutedhydrochloric acid, and extracted with hexane. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed to obtain 220 mg of2-(2-methyl-1-propenyl)phenol.

(5) Mixture of 6-chloro-3-[2-(2-methyl-1-propenyl)phenoxy]-pyridazine1-oxide and 3-chloro-6-[2-(2-methyl-1-propenyl)phenoxy]pyridazine1-oxide (Step B-2)

200 mg of 2-(2-methyl-1-propenyl)phenol obtained in (4), 1,4-dioxane (2mL) and dimethylsulfoxide (2 mL) were mixed, 151 mg (1.35 mmol) ofpotassium tert-butoxide was added to the mixture, and the resultingmixture was stirred in an ice bath for 15 minutes. To the mixture wasadded 207 mg (1.25 mmol) of 3,6-dichloropyridazine 1-oxide, and themixture was stirred in an ice bath for 15 minutes, and then, at roomtemperature for 4 hours. The reaction mixture was poured into water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (Wako gel C-100, hexane-ethylacetate, gradient) to obtain 90.0 mg (0.325 mmol, Yield from1-(2-methoxyphenyl)-2-methyl-1-propanol: 41.2%) of a mixture of6-chloro-3-[2-(2-methyl-1-propenyl)phenoxy]pyridazine 1-oxide and3-chloro-6-[2-(2-methyl-1-propenyl)phenoxy]-pyridazine 1-oxide.

(6) 4,6-Dichloro-3-[2-(2-methyl-1-propenyl)phenoxy]-pyridazine (StepB-3)

In chloroform (0.2 mL) was dissolved 90.0 mg (0.325 mmol) of a mixtureof 6-chloro-3-[2-(2-methyl-1-propenyl)phenoxy]pyridazine 1-oxide and3-chloro-6-[2-(2-methyl-1-propenyl)phenoxy]pyridazine 1-oxide obtainedin (5), 0.20 mL (2.2 mmol) of phosphorus oxychloride was mixed with theabove mixture, and the resulting mixture was stirred at 70° C. for 2hours. The reaction mixture was poured into water, extracted withdichloromethane. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by hexane:ethyl acetate=9:1) toobtain 85.0 mg (0.288 mmol, Yield: 88.6%) of4,6-dichloro-3-[2-(2-methyl-1-propenyl)phenoxy]pyridazine.

(7) 6-Chloro-3-[2-(2-methyl-1-propenyl)phenoxy]-4-pyridazinol (CompoundNo. 2540, Step A-3 and A-4)

In dimethylsulfoxide (3 mL) was dissolved 85.0 mg (0.288 mmol) of4,6-dichloro-3-[2-(2-methyl-1-propenyl)phenoxy]pyridazine obtained in(6), 122 mg (1.49 mmol) of sodium acetate was added to the solution andthe resulting mixture was stirred at 120° C. for 2 hours. The reactionmixture was cooled up to room temperature, poured into water, and madeacidic with diluted hydrochloric acid. The mixture was extracted withethyl acetate, and the organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 2 plates were used, developed by ethyl acetate) to obtain 39.6mg (0.143 mmol, Yield: 49.7%) of6-chloro-3-[2-(2-methyl-1-propenyl)phenoxy]-4-pyridazinol (Compound No.2540).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.35-7.15 (3H, m), 7.15-7.05 (1H, m),6.65 (1H, s), 6.05 (1H, s), 1.76 (3H, s), 1.70 (3H, s). Melting point (°C.): 149-152.

EXAMPLE 626 6-Chloro-3-(3-hydroxyphenoxy)-4-pyridazinol (Compound No.2544) (1) Mixture of1-{3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-phenyl}ethanone and1-{3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl}ethanone

306 mg (2.25 mmol) of 1-(3-hydroxyphenyl)ethanone, 1,4-dioxane (6 mL)and dimethylsulfoxide (6 mL) were mixed, 297 mg (2.65 mmol) of potassiumtert-butoxide was added to the mixture, and the resulting mixture wasstirred in an ice bath for 15 minutes. To the mixture was added 342 mg(2.07 mmol) of 3,6-dichloropyridazine 1-oxide in an ice bath, and theresulting mixture was stirred at room temperature for 4 hours. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, and dried over anhydrous magnesium sulfate. The solventwas removed, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate, gradient) toobtain 400 mg (1.51 mmol, Yield: 72.9%) of a mixture of1-{3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]phenyl}ethanone and1-{3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl}ethanone.

(2) Mixture of 3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-phenyl acetateand 3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl acetate

In 3 mL of dichloromethane was dissolved was dissolved 400 mg (1.51mmol) of a mixture of1-{3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]phenyl}ethanone and1-{3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl}ethanone obtained in(1), a dichloromethane (3 mL) solution containing 1.1 g (purity 70-75%,4.5-4.8 mmol) of m-chloroperbenzoic acid was added to the solution, andthe resulting mixture was stirred at room temperature for 4 days. To thereaction mixture was added a saturated aqueous sodium sulfite solution,and after stirring, the mixture was extracted with ethyl acetate. Theorganic layer was successively washed with water and brine, and driedover anhydrous sodium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel column chromatography (Wako gelC-100, hexane-ethyl acetate, gradient) to obtain 330 mg of a mixture ofthe starting material, 3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]phenylacetate, and 3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl acetate. Indichloromethane (3 mL) was dissolved 280 mg of the mixture, 1.1 g(purity 70-75%, 4.5-4.8 mmol) of m-chloroperbenzoic acid was added tothe solution, and the resulting mixture was stirred at room temperatureovernight. The reaction mixture was poured into 10% aqueous sodiumsulfite solution, and extracted with dichloromethane. The organic layerwas washed with water, and dried over anhydrous sodium sulfate. Thesolvent was removed, and the obtained residue was washed with hexane toobtain 310 mg of a mixture of3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]phenyl acetate and3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl acetate.

(3) 3-[(4,6-Dichloro-3-pyridazinyl)oxy]phenyl acetate (Step B-3)

With chloroform (0.4 mL) was mixed 310 mg of a mixture of3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]phenyl acetate and3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl acetate obtained in (2),0.40 mL (4.3 mmol) of phosphorus oxychloride was mixed with the abovemixture, and the resulting mixture was stirred at 70° C. for 3 hours.The reaction mixture was poured into water and after stirring, themixture was extracted with dichloromethane. The organic layers werecombined, washed with water, and dried over anhydrous magnesium sulfate.The solvent was removed, and the obtained residue was purified by silicagel column chromatography (Wako gel C-100, hexane-ethyl acetate,gradient) to obtain 46.0 mg (0.154 mmol, Yield from a mixture of1-{3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-phenyl}ethanone and1-{3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]phenyl}ethanone: 9.6%) of3-[(4,6-dichloro-3-pyridazinyl)oxy]phenyl acetate.

(4) 6-Chloro-3-(3-hydroxyphenoxy)-4-pyridazinol (Compound No. 2544, StepA-3 and A-4)

In dimethylsulfoxide (1 mL) was dissolved 40.0 mg (0.134 mmol) of3-[(4,6-dichloro-3-pyridazinyl)oxy]phenyl acetate obtained in (3), 56.0mg (0.683 mmol) of sodium acetate was added to the solution and theresulting mixture was stirred at 120° C. for 1 hour. After cooling up toroom temperature, the reaction mixture was poured into 0.5 mol/L aqueoussodium hydroxide solution, and washed with ethyl acetate. The aqueouslayer was made acidic with 4 mol/L hydrochloric acid, and extracted withethyl acetate. The organic layers were combined, washed successivelywith water and brine. After drying over anhydrous magnesium sulfate, thesolvent was removed to obtain 30 mg (0.126 mmol, Yield: 94.0%) of6-chloro-3-(3-hydroxyphenoxy)-4-pyridazinol (Compound No. 2544).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.25-7.10 (1H, m), 6.70-6.57 (4H, m).Melting point (° C.): 248-251.

EXAMPLE 627 6-Chloro-3-(2-iodo-3-methoxyphenoxy)-4-pyridazinol (CompoundNo. 2551) (1) 1-Methoxy-3-(methoxymethoxy)benzene

In N,N-dimethylformamide(50 mL) was dissolved 3.68 g (29.7 mmol) ofcommercially available 3-methoxyphenol, 1.81 g (45.4 mmol) of 60% sodiumhydride was added to the solution in an ice bath, and the resultingmixture was stirred in an ice bath for 20 minutes. To the mixture wasgradually added dropwise in an ice bath 4.05 mL (53.3 mmol) ofchloro(methoxy)methane, and the resulting mixture was stirred at roomtemperature overnight. To the reaction mixture was added a saturatedaqueous ammonium chloride solution, and the mixture was extracted withethyl acetate. The organic layer was successively washed with water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate, gradient) toobtain 4.81 g (28.6 mmol, Yield: 96.3%) of1-methoxy-3-(methoxymethoxy)benzene.

(2) 2-Iodo-1-methoxy-3-(methoxymethoxy)benzene

In dry ether (50 mL) was dissolved 3.70 g (22.0 mmol) of1-methoxy-3-(methoxymethoxy)benzene obtained in (1), the solution wascooled to −78° C. under nitrogem atmosphere, and 5.60 mL (37.2 mmol) oftetramethylethylenediamine, then, 22.0 mL (35.2 mmol) of n-butyllithium-hexane solution (1.60 M) were added to the solution. Theresulting mixture was stirred at −78° C. for 30 minutes, then at 0C for30 minutes, and cooled to −78° C., 9.80 g (38.6 mmol) of iodine wasadded to the mixture. The mixture was stirred at −78° C. for 30 minutes,a saturated aqueous ammonium chloride solution was added to the reactionmixture, and the mixture was extracted with ethyl acetate. The organiclayer was washed with a saturated aqueous sodium thiosulfate solution,and dried over anhydrous magnesium sulfate. The solvent was removed toobtain 6.59 g of 2-iodo-1-methoxy-3-(methoxymethoxy)benzene.

(3) 2-Iodo-3-methoxyphenol

In methanol (70 mL) was dissolved 6.59 g of2-iodo-1-methoxy-3-(methoxymethoxy)benzene obtained in (2), conc.hydrochloric acid (0.18 mL) was added dropwise to the solution, and theresulting mixture was stirred at 65° C. for 1 hour and 15 minutes.Moreover, conc. hydrochloric acid (0.20 mL) was additionally addedthereto, and the resulting mixture was stirred at 65° C. for 2 hours and40 minutes. The reaction mixture was poured into water, and extractedwith ethyl acetate. The organic layer was washed with brine, and driedover anhydrous magnesium sulfate. The solvent was removed, and theobtained residue was purified by silica gel column chromatography (Wakogel C-100, hexane-ethyl acetate, gradient) to obtain 4.61 g (18.4 mmol,Yield from 1-methoxy-3-(methoxymethoxy)benzene: 83.6%) of2-iodo-3-methoxyphenol.

(4) Mixture of 6-chloro-3-(2-iodo-3-methoxyphenoxy)pyridazine 1-oxideand 3-chloro-6-(2-iodo-3-methoxyphenoxy)pyridazine 1-oxide (Step B-2)

298 mg (1.19 mmol) of 2-iodo-3-methoxyphenol obtained in (3),1,4-dioxane (2.5 mL) and dimethylsulfoxide (2.5 mL) were mixed, 215 mg(1.92 mmol) of potassium tert-butoxide was added to the mixture, and theresulting mixture was stirred in an ice bath for 10 minutes. To themixture was added 196 mg (1.19 mmol) of 3,6-dichloropyridazine 1-oxidein an ice bath, and the resulting mixture was stirred at at roomtemperature for 3 days. To the reaction mixture was added a saturatedaqueous ammonium chloride solution, and the mixture was extracted withethyl acetate. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (developed by hexane:ethylacetate=3:1, then, hexane:ethyl acetate=1:1) to obtain 324 mg (0.855mmol, Yield: 71.8%) of a mixture of6-chloro-3-(2-iodo-3-methoxyphenoxy)pyridazine 1-oxide and3-chloro-6-(2-iodo-3-methoxyphenoxy)pyridazine 1-oxide.

(5) 4,6-Dichloro-3-(2-iodo-3-methoxyphenoxy)pyridazine (Step B-3)

1.0 mL (1.1 mmol) of phosphorus oxychloride was added to 324 mg (0.855mmol) of a mixture of 6-chloro-3-(2-iodo-3-methoxyphenoxy)pyridazine1-oxide and 3-chloro-6-(2-iodo-3-methoxyphenoxy)pyridazine 1-oxideobtained in (4), and the resulting mixture was stirred at roomtemperature overnight. The reaction mixture was poured into water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with a saturated aqueous sodium hydrogen carbonate solutionand brine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate=5:1) to obtain 225mg (0.567 mmol, Yield: 66.3%) of4,6-dichloro-3-(2-iodo-3-methoxyphenoxy)pyridazine.

(6) 6-Chloro-3-(2-iodo-3-methoxyphenoxy)-4-pyridazinol (Compound No.2551, Step A-3 and A-4)

In dimethylsulfoxide (2 mL) was dissolved 105 mg (0.264 mmol) of4,6-dichloro-3-(2-iodo-3-methoxyphenoxy)-pyridazine obtained in (5), 118mg (1.44 mmol) of sodium acetate was added to the solution and theresulting mixture was stirred at 120° C. for 1 hour and 30 minutes.After cooling the mixture up to room temperature, 4 mol/L hydrochloricacid was added to the reaction mixture, and the mixture was extractedwith ethyl acetate. The organic layers were combined, and washed withbrine. After drying over anhydrous magnesium sulfate, the solvent wasremoved, and the obtained residue was washed with isopropyl ether toobtain 51.2 mg (0.135 mmol, Yield: 51.1%) of6-chloro-3-(2-iodo-3-methoxyphenoxy)-4-pyridazinol (Compound No. 2551).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.39 (1H, t, J=8.4 Hz), 6.84 (2H, br.t,J=8.4 Hz), 6.73 (1H, s), 3.90 (3H, s). Melting point (° C.): 231-234.

EXAMPLE 6286-Chloro-3-{[7-(3-hydroxypropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}-4-pyridazinol(Compound No. 2555) (1) 2-Iodo-3-methoxyphenyl trifluoromethanesulfonate

In dry dichloromethane was dissolved 3.75 g (15.0 mmol) of2-iodo-3-methoxyphenol obtained in Example 627(3), and 7.28 mL (90.0mmol) of pyridine was added to the solution. The mixture was cooled to−20° C., 5.40 mL (32.2 mmol) of trifluoromethanesulfonic anhydride wasadded thereto, and the resulting mixture was stirred for 3 hours and 50minutes. The reaction mixture was poured into water, and extracted withdichloromethane, then with ethyl acetate. The organic layers werecombined, washed successively with 4 mol/L hydrochloric acid, water andbrine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate=10:1) to obtain5.52 g (14.5 mmol, Yield: 96.7%) of 2-iodo-3-methoxyphenyltrifluoromethanesulfonate.

(2)tert-Butyl[(8-methoxy-2,3,4,4a-tetrahydro-8bH-benzo-[3,4]cyclobuta[1,2-b]pyran-8b-yl)oxy]dimethylsilane

In dry tetrahydrofuran (15 mL) was dissolved 1.10 g (2.88 mmol) of2-iodo-3-methoxyphenyl trifluoromethanesulfonate obtained in (1), and1.00 mL (4.37 mmol) of commercially availabletert-butyl(3,4-dihydro-2H-pyran-6-yloxy)dimethylsilane was added to thesolution under nitrogen atmosphere. The mixture was cooled to −78° C.,4.50 mL (7.20 mmol) of n-butyl lithium-hexane solution (1.60 M) wasadded to the mixture and the resulting mixture was stirred for 20minutes. The reaction mixture was poured into a buffer (prepared bydissolving 9.1 g of KH₂PO₄ and 4.3 g of Na₂HPO₄ in 1 L of water) with apH of 7, and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (Wako gel C-100,hexane-ethyl acetate=50:1) to obtain 0.897 g (2.79 mmol, Yield: 96.9%)of tert-butyl[(8-methoxy-2,3,4,4a-tetrahydro-8bH-benzo[3,4]cyclobuta[1,2-b]pyran-8b-yl)oxy]dimethylsilane.

(3) 8-(3-Hydroxypropyl)-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one

In acetonitrile (12 mL) was dissolved 897 mg (2.79 mmol) oftert-butyl[(8-methoxy-2,3,4,4a-tetrahydro-8bH-benzo[3,4]cyclobuta[1,2-b]pyran-8b-yl)oxy]dimethylsilane obtained in(2), 0.30 mL (7.96-8.30 mmol) of 46-47% hydrofluoric acid aqueoussolution was added to the solution in an ice bath, and the resultingmixture was stirred for 30 minutes. The reaction mixture was poured intoa saturated aqueous sodium hydrogen carbonate solution, and extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was removed, and the residue was purified by silicagel column chromatography (Wako gel C-100, hexane-ethyl acetate=7:3) toobtain 446 mg (2.17 mmol, Yield: 77.8%) of8-(3-hydroxypropyl)-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one.

(4) 8-(3-Chloropropyl)-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one

In dichloromethane (22 mL) was dissolved 474 mg (2.30 mmol) of8-(3-hydroxypropyl)-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-oneobtained in (3), 467 mg (3.49 mmol) of N-chlorosuccinimide and 917 mg(3.5 mmol) of triphenylphosphine were added to the solution, and theresulting mixture was stirred at room temperature for 1 hour. Thereaction mixture was poured into water, a saturated aqueous sodiumhydrogen carbonate solution was added thereto, and the mixture wasextracted with ethyl acetate. The organic layers were combined, washedwith brineand dried over anhydrous magnesium sulfate. The solvent wasremoved, and the residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate=20:1) to obtain 409mg (1.82 mmol, Yield: 79.1%) of8-(3-chloropropyl)-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-one.

(5) 7-(3-Chloropropyl)-2-methoxybicyclo[4.2.0]octa-1,3,5-triene

Water (6 mL) was added to 111 mg (0.408 mmol) of mercury chloride(HgCl₂) to dissolve therein, 4.00 g (6.12 mmol) of zinc powder was addedto the solution and the resulting mixture was stirred at roomtemperature for 50 minutes. After removing the supernatant, the remainedsolid was washed once with water. To the material were gradually addedwater (6.0 mL), and then, conc. hydrochloric acid (5.0 mL), and furtheradded acetic acid (2.4 mL), and finally 409 mg (1.82 mmol) of8-(3-chloropropyl)-5-methoxybicyclo[4.2.0]octa-1,3,5-trien-7-oneobtained in (4) dissolved in toluene (2 mL) and ethanol (2 mL). Themixture was stirred at 115° C. overnight, and cooled up to roomtemperature. Toluene (20 mL) was added to the mixture and the resultingmixture was stirred at 30 minutes, and the organic layer was separated.The obtained organic layer was washed with water, and dried overanhydrous magnesium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (Wako gel C-100,hexane-ethyl acetate=20:1) to obtain 304 mg (1.44 mmol, Yield: 79.1%) of7-(3-chloropropyl)-2-methoxybicyclo[4.2.0]octa-1,3,5-triene.

(6) 7-(3-Chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-ol

In dichloromethane(2.0 mL) was dissolved 304 mg (1.44 mmol) of7-(3-chloropropyl)-2-methoxybicyclo[4.2.0]octa-1,3,5-triene obtained in(5), 0.50 mL (5.32 mmol) of boron tribromide was added to the solutionin an ice bath with stirring, and the resulting mixture was stirred inan ice bath for 1 hour. The reaction mixture was poured into ice-waterand extracted with ethyl acetate. The organic layers were combined,washed with brineand dried over anhydrous magnesium sulfate. The solventwas removed, and the residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate=4:1) to obtain 303mg (1.54 mmol, Yield: quantitative) of7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-ol.

(7) Mixture of6-chloro-3-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine1-oxide and3-chloro-6-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine1-oxide (Step B-2)

303 mg (1.54 mmol) of7-(3-chloropropyl)bicycle[4.2.0]octa-1,3,5-trien-2-ol obtained in (6),1,4-dioxane (2.0 mL) and dimethylsulfoxide (2.0 mL) were mixed, 275 mg(2.46 mmol) of potassium tert-butoxide was added to the mixture, and theresulting mixture was stirred in an ice bath for 10 minutes. To themixture was added 254 mg (1.54 mmol) of 3,6-dichloropyridazine 1-oxidein an ice bath, and the resulting mixture was stirred at roomtemperature overnight. To the reaction mixture was added a saturatedaqueous ammonium chloride solution, and the mixture was extracted withethyl acetate. The organic layers were combined, washed successivelywith water and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (developed by hexane:ethylacetate=3:1) to obtain 364 mg (1.12 mmol, Yield: 72.7%) of a mixture of6-chloro-3-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine1-oxide and3-chloro-6-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine1-oxide.

(8)4,6-Dichloro-3-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine(Step B-3)

1.0 mL (11 mmol) of phosphorus oxychloride was added to 364 mg (1.12mmol) of a mixture of6-chloro-3-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine1-oxide and3-chloro-6-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine1-oxide obtained in (7), and the resulting mixture was stirred at roomtemperature for 7 hours and 15 minutes. The reaction mixture was pouredinto water, and extracted with ethyl acetate. The organic layers werecombined, washed successively with a saturated aqueous sodium hydrogencarbonate solution and brine, and dried over anhydrous magnesiumsulfate. The solvent was distilled off and the residue was purified bypreparative thin-layer chromatography (developed by hexane:ethylacetate=2:1) to obtain 253 mg (0.735 mmol, Yield: 65.6%) of4,6-dichloro-3-{[7-(3-chloropropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazine.

(9)6-Chloro-3-{[7-(3-hydroxypropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}-4-pyridazinol(Compound No. 2555, Step A-3 and A-4)

In dimethylsulfoxide (5.0 mL) was dissolved 253 mg (0.735 mmol) of4,6-dichloro-3-{[7-(3-chloropropyl)bicycle[4.2.0]octa-1,3,5-trien-2-yl]oxy}pyridazineobtained in (8), 250 mg (3.05 mmol) of sodium acetate was added to thesolution and the resulting mixture was stirred at 120° C. for 2 hours.After cooling up to room temperature, 4 mol/L hydrochloric acid wasadded to the reaction mixture, and the mixture was extracted with ethylacetate. The organic layers were combined, and washed with brine. Afterdrying over anhydrous magnesium sulfate, the solvent was distilled offand the obtained residue was purified by preparative thin-layerchromatography (developed by hexane:ethyl acetate=2:1) to obtain 48.5 mg(0.158 mmol, Yield: 21.5%) of6-chloro-3-{[7-(3-hydroxypropyl)bicyclo[4.2.0]octa-1,3,5-trien-2-yl]oxy}-4-pyridazinol(Compound No. 2555). Also, 28.2 mg of a mixture of6-chloro-3-{[7-(3-chloropropyl)bicycle[4.2.0]octa-1,3,5-trien-2-yl]oxy}-4-pyridazinoland3-{2-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]bicyclo[4.2.0]octa-1,3,5-trien-7-yl}propylacetate was obtained.

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.22-7.18 (1H, m), 6.98-6.94 (2H, m),6.70 (1H, s), 3.62-3.56 (2H, m), 3.46 (1H, br.s), 3.34 (1H, br.s), 3.18(1H, dd, J=13.9, 5.5 Hz), 2.62 (1H, dd, J=13.9, 2.2 Hz), 1.81-1.62 (4H,m). Appearance: oily product.

EXAMPLE 6296-Chloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]-4-pyridazinol(Compound No. 2556) (1)5-Methoxy-8,8-dimethylbicyclo[4.2.0]octa-1,3,5-trien-7-one

In dry tetrahydrofuran(10 mL) was dissolved 723 mg (1.89 mmol) of2-iodo-3-methoxyphenyl trifluoromethanesulfonate obtainable by themethod of Example 628(1), and 0.50 mL (2.47 mmol) of commerciallyavailable [(1-methoxy-2-methyl-1-propynyl)oxy](trimethyl)silane wasadded to the solution under nitrogen atmosphere. The mixture was cooledto −78° C., 2.70 mL (4.32 mmol) of n-butyl lithium-hexane solution(1.60M) was added thereto and the resulting mixture was stirred for 20minutes. The reaction mixture was poured into a buffer (prepared bydissolving 9.1 g of KH₂PO₄ and 4.3 g of Na₂HPO₄ in 1 L of water) with apH of 7, and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and to the residuewere added tetrahydrofuran (2.0 mL), water (0.2 mL) and acetic acid (2.0mL), and the resulting mixture was stirred at room temperature for 1hour. Ether was added to the reaction mixture, and the mixture waswashed successively with a saturated aqueous sodium hydrogen carbonatesolution and brine, and dried over anhydrous magnesium sulfate. Thesolvent was distilled off and the residue was purified by preparativethin-layer chromatography (developed by hexane:ethyl acetate=2:1) toobtain 182 mg (1.03 mmol, Yield: 54.5%) of5-methoxy-8,8-dimethylbicyclo[4.2.0]octa-1,3,5-trien-7-one.

(2) 2-Methoxy-7,7-dimethylbicyclo[4.2.0]octa-1,3,5-triene

Water (6 mL) was added to 109 mg (0.401 mmol) of mercury chloride(HgCl₂) to dissolve therein, 3.98 g (6.09 mmol) of zinc powder was addedthereto and the resulting mixture was stirred at room temperature for 1hour. The supernatant was removed, and the remained solid was washedonce with water. To the material were gradually added water (6.0 mL),then conc. hydrochloric acid (5.0 mL), and further acetic acid(2.4 mL),and finally 182 mg (1.03 mmol) of5-methoxy-8,8-dimethylbicyclo[4.2.0]octa-1,3,5-trien-7-one obtained in(1) dissolved in toluene (2 mL) and ethanol (2 mL). The resultingmixture was stirred at 115° C. over-night, and cooled up to roomtemperature. Toluene (20 mL) was added to the mixture and the mixturewas stirred for 20 minutes, and the organic layer was separated. Theobtained organic layer was washed with water, and dried over anhydrousmagnesium sulfate. The solvent was distilled off and the residue waspurified by preparative thin-layer chromatography (developed byhexane:ethyl acetate=25:1) to obtain 85.1 mg (0.525 mmol, Yield: 51.0%)of 2-methoxy-7,7-dimethylbicyclo[4.2.0]octa-1,3,5-triene.

(3) 7,7-Dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-ol

In dichloromethane(5.0 mL) was dissolved 85.1 mg (0.525 mmol) of2-methoxy-7,7-dimethylbicyclo[4.2.0]octa-1,3,5-triene obtained in (2),0.20 mL (2.12 mmol) of boron tribromide was added to the solution in anice bath with stirring, and the resulting mixture was stirred in an icebath for 2 hours and 10 minutes. The reaction mixture was poured intoice-water and extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed to obtain 97.6 mgof 7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-ol.

(4)6-Chloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine1-oxide and3-chloro-6-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine1-oxide (Step B-2)

97.6 mg of 7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-ol obtained in(3), 1,4-dioxane (1.5 mL) and dimethylsulfoxide (1.5 mL) were mixed,97.8 mg (0.873 mmol) of potassium tert-butoxide was added to thesolution, and the resulting mixture was stirred in an ice bath for 10minutes. To the mixture was added 90.2 mg (0.547 mmol) of3,6-dichloropyridazine 1-oxide in an ice bath, and the mixture wasstirred at room temperature overnight. To the reaction mixture was addeda saturated aqueous ammonium chloride solution, and the mixture wasextracted with ethyl acetate. The organic layers were combined, washedwith brineand dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the obtained residue was purified by preparativethin-layer chromatography (developed by hexane:ethyl acetate=3:1 twotimes) to obtain 61.7 mg (0.223 mmol, Yield from2-methoxy-7,7-dimethylbicyclo[4.2.0]octa-1,3,5-triene: 42.5%) of amixture of6-chloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine1-oxide and3-chloro-6-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]-pyridazine1-oxide.

(5)4,6-Dichloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine(StepB-3)

0.50 mL (5.4 mmol) of phosphorus oxychloride was added to 61.7 mg (0.223mmol) of a mixture of6-chloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]-pyridazine1-oxide and3-chloro-6-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine1-oxide obtained in (4), and the resulting mixture was stirred at roomtemperature overnight. The reaction mixture was poured into water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with a saturated aqueous sodium hydrogen carbonate solutionand brine, and dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the residue was purified by preparative thin-layerchromatography (developed by hexane:ethyl acetate=5:1) to obtain 43.7 mg(0.148 mmol, Yield: 66.4%) of4,6-dichloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazine.

(6)6-Chloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]-4-pyridazinol(Compound No. 2556, Step A-3 and Step A-4)

In dimethylsulfoxide(2.0 mL) was dissolved 43.7 mg (0.148 mmol) of4,6-dichloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]pyridazineobtained in (5), 63.1 mg (0.770 mmol) of sodium acetate was added to thesolution and the resulting mixture was stirred at 120° C. for 2 hours.After cooling up to room temperature, 4 mol/L hydrochloric acid wasadded to the reaction mixture, and extracted with ethyl acetate. Theorganic layers were combined, washed successively with water and brine.After drying over anhydrous magnesium sulfate, the solvent was removed,and the obtained residue was washed with isopropyl ether to obtain 31.6mg (0.114 mmol, Yield: 77.0%) of6-chloro-3-[(7,7-dimethylbicyclo[4.2.0]octa-1,3,5-trien-2-yl)oxy]-4-pyridazinol(Compound No. 2556).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.26-7.19 (1H, m), 6.97-6.89 (2H, m),6.71 (1H, s), 2.81 (2H, s), 1.41 (6H, s). Melting point (° C.): 197-199.

EXAMPLE 630 4-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-3-methylphenylacetate (Compound No. 2572) (1) Mixture of1-{4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenyl}ethanone and1-{4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenyl}ethanone (StepB-2)

784 mg (5.23 mmol) of commercially available1-(4-hydroxy-3-methylphenyl)ethanone, 1,4-dioxane (5 mL) anddimethylsulfoxide (5 mL) were mixed, 938 mg (8.38 mmol) of potassiumtert-butoxide was added to the mixture and the resulting mixture wasstirred in an ice bath for 10 minutes. To the mixture was added 861 mg(5.22 mmol) of 3,6-dichloropyridazine 1-oxide in an ice bath, and themixture was stirred at room temperature overnight. To the reactionmixture was added a saturated aqueous ammonium chloride solution, andthe mixture was extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (Wako gel C-100,hexane-ethyl acetate=5:1) to obtain 758 mg (2.74 mmol, Yield: 52.5%) ofa mixture of1-{4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenyl}ethanone and1-{4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenyl}ethanone.

(2) Mixture of 4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenylacetate and 4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenylacetate

In 1,2-dichloroethane (13 mL) was dissolved 758 mg (2.74 mmol) of amixture of1-{4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenyl}ethanone and1-{4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenyl}ethanoneobtained in (1), a dichloromethane (3 mL) solution containing 1.1 g(purity 70-75%, 4.5-4.8 mmol) of m-chloroperbenzoic acid was added tothe solution, and the resulting mixture was stirred at room temperaturefor 4 hours and 45 minutes. Moreover, 1.20 g (purity 70-75%, 4.86-5.20mmol) of m-chloroperbenzoic acid was added to the mixture, and themixture was stirred at room temperature overnight. The reaction mixturewas poured into 10% aqueous sodium sulfite solution, and extracted withethyl acetate. The organic layer was washed successively with asaturated aqueous sodium carbonate and brine, and dried over anhydroussodium sulfate. The solvent was removed, and the residue was purified bysilica gel column chromatography (Wako gel C-100, hexane-ethylacetate=5:1) to obtain the starting material and 330 mg of a mixture of3-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-phenyl acetate and3-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-phenyl acetate. Indichloromethane (3 mL) was dissolved 280 mg of the mixture, 2.62 g(purity 70-75%, 10.6-11.4 mmol) of m-chloroperbenzoic acid was added tothe solution, and the resulting mixture was stirred at room temperaturefor 4 hours and 45 minutes. Moreover, 1.20 g (purity 70-75%, 4.86-5.20mmol) of m-chloroperbenzoic acid was added to the mixture, and themixture was stirred at room temperature overnight. The reaction mixturewas poured into 10% aqueous sodium sulfite solution, and extracted withethyl acetate. The organic layer was washed successively with asaturated aqueous sodium carbonate and a saturated saline solution, anddried over anhydrous sodium sulfate. The solvent was removed, and theresidue was purified by silica gel column chromatography (Wako gelC-100, hexane-ethyl acetate=5:1) to obtain the starting material and 622mg of a mixture of4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate and4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate. 0.5 mL(4.85 mmol) of 30% hydrogen peroxide aqueous solution was mixed with1,2-dichloroethane (2.2 mL), 3.2 mL (22.7 mmol) of trifluoroaceticanhydride was added dropwise thereto in an ice bath, and the resultingmixture was stirred at room temperature. In an ice bath, this mixturewas added to the mixture of the starting material,4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate, and4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate, whichwas previously obtained and dissolved in 1,2-dichloroethane (2.2 mL),and the resulting mixture was stirred in an ice bath for 1 hour, and atroom temperature overnight. The reaction mixture was poured into 10%aqueous sodium sulfite solution, and extracted with ethyl acetate. Theorganic layer was washed successively with a saturated aqueous sodiumcarbonate, water and brine, and dried over anhydrous sodium sulfate. Thesolvent was removed, and the residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate gradient) to obtain413 mg (1.40 mmol, Yield: 51.1%) of a mixture of4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate and4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate.

(3) 4-[(4,6-Dichloro-3-pyridazinyl)oxy]-3-methylphenyl acetate (StepB-3)

In chloroform(2 mL) was dissolved 413 mg (1.40 mmol) of a mixture of4-[(6-chloro-1-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate and4-[(6-chloro-2-oxide-3-pyridazinyl)oxy]-3-methylphenyl acetate obtainedin (2), 2.0 mL (22 mmol) of phosphorus oxychloride was mixed with thesolution, and the resulting mixture was stirred at 80° C. for 3 hours.The reaction mixture was diluted with dichloromethane, and then, pouredinto water. The mixture was extracted with dichloromethane, and then,with ethyl acetate. The organic layers were combined, washedsuccessively with a saturated aqueous sodium hydrogen carbonate solutionand brine, and dried over anhydrous magnesium sulfate. The solvent wasremoved, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane-ethyl acetate, hexane-ethylacetate=6:1) to obtain 336 mg (1.07 mmol, Yield: 76.4%) of4-[(4,6-dichloro-3-pyridazinyl)oxy]-3-methylphenyl acetate.

(4) 4-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]-3-methylphenyl acetate(Compound No. 2572, Step A-3 and Step A-4)

In dimethylsulfoxide (1.5 mL) was dissolved 160 mg (0.511 mmol) of4-[(4,6-dichloro-3-pyridazinyl)oxy]-3-methylphenyl acetate obtained in(3), 136 mg (1.66 mmol) of sodium acetate was added to the solution andthe resulting mixture was stirred at 120° C. for 2 hours. After coolingup to room temperature, 4 mol/L hydrochloric acid was added to thereaction mixture, and the mixture was extracted with ethyl acetate. Theorganic layers were combined, washed successively with water and brine.After drying over anhydrous magnesium sulfate, the solvent was removed,and the obtained residue was washed with isopropyl ether to obtain 37.3mg (0.126 mmol, Yield: 24.7%) of4-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]-3-methylphenyl acetate(Compound No. 2572).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.13-6.94 (3H, m), 6.70 (1H, s), 2.27(3H, s), 2.17 (3H, s). Melting point (° C.): 255 (dec.).

EXAMPLE 6316-Chloro-3-[2-(difluoromethyl)-6-methylphenoxy]-4-pyridazinol (CompoundNo. 2576) (1) 2-(methoxymethoxy)-3-methylbenzaldehyde

In N,N-dimethylformamide(50 mL) was dissolved 4.96 g (36.5 mmol) of2-hydroxy-3-methylbenzaldehyde, 2.19 g (54.6 mmol) of 60% sodium hydridewas added to the solution in an ice bath and the resulting mixture wasstirred for 10 minutes. To the mixture was added 3.59 mL (47.3 mmol) ofchloro(methoxy)methane in an ice bath, and the resulting mixture wasstirred at room temperature for 1 hour and 30 minutes. The reactionmixture was poured into a saturated aqueous ammonium chloride solution,and extracted with ethyl acetate. The organic layers were combined,washed successively with water and brine, and dried over anhydroussodium sulfate. The solvent was removed, and the residue was purified bysilica gel column chromatography (Daisogel 1001W, hexane:ethylacetate=50:1) to obtain 6.60 g (36.6 mmol, Yield: 100%) of2-(methoxymethoxy)-3-methylbenzaldehyde.

(2) 1-(Difluoromethyl)-2-(methoxymethoxy)-3-methylbenzene

In dichloromethane(10 mL) was dissolved 589 mg (3.27 mmol) of2-(methoxymethoxy)-3-methylbenzaldehyde obtained in (1), 0.863 mL (6.52mmol) of (diethylamino)sulfur trifluoride (DAST) was added to thesolution under nitrogen atmosphere, and the resulting mixture wasstirred at room temperature for 3 hours. After allowing to stand at roomtemperature overnight, the reaction mixture was poured into water, andextracted with dichloromethane. The organic layers were combined, washedwith water, and dried over anhydrous sodium sulfate. The solvent wasremoved, and the residue was purified by silica gel columnchromatography (Daisogel 1001W, hexane:ethyl acetate=10:1) to obtain 229mg (1.13 mmol, Yield: 34.6%) of1-(difluoromethyl)-2-(methoxymethoxy)-3-methylbenzene.

(3) 2-(Difluoromethyl)-6-methylphenol

In methanol (5 mL) was dissolved 229 mg (1.13 mmol) of1-(difluoromethyl)-2-(methoxymethoxy)-3-methylbenzene obtained in (2),two drops of conc. hydrochloric acid was added to the solution at roomtemperature and the resulting mixture was stirred at 60° C. for 30minutes. The reaction mixture was cooled to room temperature, and thesolvent was removed under reduced pressure. Ethyl acetate was added tothe residue, and the mixture was washed with brineand dried overanhydrous sodium sulfate. The solvent was removed to obtain 135 mg(0.854 mmol, Yield: 75.6%) of 2-(difluoromethyl)-6-methylphenol.

(4) 6-Chloro-3-[2-(difluoromethyl)-6-methylphenoxy]pyridazine 1-oxideand 3-chloro-6-[2-(difluoromethyl)-6-methylphenoxy]pyridazine 1-oxide(Step B-1)

In 1,4-dioxane (1.5 mL) and dimethylsulfoxide (1.5 mL) was dissolved 135mg (0.854 mmol) of 2-(difluoromethyl)-6-methylphenol obtained in (3),115 mg (1.03 mmol) of potassium tert-butoxide was added to the mixturein an ice bath, and the resulting mixture was stirred for 5 minutes. Tothe mixture was added 141 mg (0.855 mmol) of 3,6-dichloropyridazine1-oxide in an ice bath, and the mixture was stirred at room temperatureovernight. The reaction mixture was poured into water, and extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (eluted by hexane:ethyl acetate=2:1)and by preparative thin-layer chromatography (available from MERCK CO.,1.05744, 3 plates were used, developed by hexane:ethyl acetate=2:1) toobtain 28.6 mg (0.0997 mmol, Yield: 11.7%) of a mixture of6-chloro-3-[2-(difluoromethyl)-6-methylphenoxy]pyridazine 1-oxide and3-chloro-6-[2-(difluoromethyl)-6-methylphenoxy]pyridazine 1-oxide.

(5) 4,6-Dichloro-3-[2-(difluoromethyl)-6-methylphenoxy]pyridazine(StepB-3)

In chloroform(0.5 mL) was dissolved 28.6 mg (0.0997 mmol) of a mixtureof 6-chloro-3-[2-(difluoromethyl)-6-methylphenoxy]pyridazine 1-oxide and3-chloro-6-[2-(difluoromethyl)-6-methylphenoxy]pyridazine 1-oxideobtained in (4), 76.5 mg (0.50 mmol) of phosphorus oxychloride was addedto the solution and the resulting mixture was refluxed for 8 hours.After allowing to stand at room temperature overnight, water anddichloromethane were added to the reaction mixture, and the resultingmixture was stirred for 30 minutes. The mixture was extracted withdichloromethane, the organic layers were combined, washed with water,and dried over anhydrous sodium sulfate. The solvent was distilled offand the residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, developed by hexane:ethylacetate=4:1) to obtain 19.1 mg (0.0626 mmol, Yield: 62.8%) of4,6-dichloro-3-[2-(difluoromethyl)-6-methylphenoxy]pyridazine.

(6) 6-Chloro-3-[2-(difluoromethyl)-6-methylphenoxy]-4-pyridazinol(Compound No. 2576)

In dimethylsulfoxide(0.5 mL) was dissolved 19.1 mg (0.0626 mmol) of4,6-dichloro-3-[2-(difluoromethyl)-6-methylphenoxy]pyridazine obtainedin (5), 25.7 mg (0.313 mmol) of sodium acetate was added to the solutionand the resulting mixture was stirred at 120° C. for 2 hours. Aftercooling up to room temperature, water was added to the reaction mixture,and the mixture was extracted with ethyl acetate. The organic layerswere combined, washed successively with water and brine. After dryingover anhydrous sodium sulfate, the solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, developed by ethyl acetate) toobtain 17.8 mg (0.0620 mmol, Yield: 99.0%) of6-chloro-3-[2-(difluoromethyl)-6-methylphenoxy-4-pyridazinol (CompoundNo. 2576).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.55-7.25 (3H, m), 6.83 (1H, t, J=55.1Hz). 2.15 (3H, s). Melting point (° C.): 204-205.

EXAMPLE 6326-Chloro-3-[2,4-dibromo-5-(ethylsulfanyl)phenoxy]-4-pyridazinol(Compound No. 2596) (1)4,6-Dichloro-3-[2,4-dibromo-5-(ethylsulfanyl)phenoxy]pyridazine

2.05 g (8.84 mmol) of commercially available1-bromo-2-methoxy-4-nitrobenzene and water (200 mL) were mixed, and 11.4g (213 mmol) of ammonium chloride, then 4.78 g (73.2 mmol) of zincpowder were added to the mixture. After stirring at room temperature for5 hours, the mixture was filtered through Celite, and the filtrate wasextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was removed to obtain 1.78 g of the residue.

The residue was mixed with water (9 mL) and 47% hydrobromic acid aqueoussolution (3 mL), an aqueous solution (3.6 mL of water) containing 655 mg(9.49 mmol) of sodium nitrite was added dropwise to the mixture in anice bath with stirring. After completion of the dropwise addition, themixture was stirred for 10 minutes, and 973 mg (6.80 mmol) of cuprousbromide dissolved in 47% hydrobromic acid aqueous solution (3.6 mL) wasadded dropwise to the mixture. The reaction mixture was stirred at 110°C. for 2 hours and 30 minutes, then cooled up to room temperature, waterwas added thereto and the mixture was extracted with ethyl acetate. Theorganic layers were combined, washed successively with water and brine,and dried over anhydrous magnesium sulfate. The solvent was removed, andthe obtained residue was purified by silica gel column chromatography(Wako gel C-100, hexane: ethyl acetate=10:1) and by preparativethin-layer chromatography (available from MERCK CO., 1.05717, developedmultiply by hexane:ethyl acetate=4:1) to obtain 751 mg of a crudeproduct.

Under nitrogen atmosphere, in dry N,N-dimethylformamide (5 mL) wassuspended 339 mg (8.46 mmol) of 60% sodium hydride, and 0.65 mL (8.78mmol) of ethanethiol was gradually added dropwise to the suspension.After stirring for 30 minutes, 751 mg of the previously obtained crudeproduct dissolved in N,N-dimethylformamide (8 mL) was added to themixture, and the resulting mixture was stirred at 160° C. for 5 hours.After the reaction mixture was allowed to stand at room temperatureovernight, it was poured into water, made acidic by adding dilutedhydrochloric acid, and extracted with ethyl acetate. The organic layerswere combined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theobtained residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 3 plates were used, developedmultiply by hexane:ethyl acetate=4:1) to obtain 109 mg of a phenoliccrude product.

109 mg of the obtained phenolic crude product was mixed with 1,4-dioxane(3 mL) and dimethylsulfoxide (3 mL), 53.5 mg (0.478 mmol) of potassiumtert-butoxide was added to the mixture, and the resulting mixture wasstirred in an ice bath for 15 minutes. To the mixture was added 71.2 mg(0.432 mmol) of 3,6-dichloropyridazine 1-oxide in an ice bath, and theresulting mixture was stirred at room temperature overnight. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, and dried over anhydrous magnesium sulfate. The solventwas distilled off and the obtained residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 3 plateswere used, developed multiply by hexane:ethyl acetate=2:1) to obtain71.5 mg of an etheric crude product.

In phosphorus oxychloride (3 mL) was dissolved 44.8 mg of the ethericcrude product, and the resulting mixture was stirred at 60° C. for 21hours. Water and dichloromethane were added to the reaction mixture andafter stirring, the mixture was extracted with dichloromethane. Theorganic layers were combined, washed with water, and dried overanhydrous magnesium sulfate. The solvent was distilled off and theresidue was purified by preparative thin-layer chromatography (availablefrom MERCK CO., 1.05744, 2 plates were used, developed by hexane:ethylacetate=2:1) to obtain 14.4 mg (0.0314 mmol, Yield: 0.567%) of4,6-dichloro-3-[2,4-dibromo-5-(ethylsulfanyl)phenoxy]pyridazine.

(2) 6-Chloro-3-[2,4-dibromo-5-(ethylsulfanyl)phenoxy]-4-pyridazinol(Compound No. 2596, Step A-3 and A-4)

In dimethylsulfoxide (3 mL) was dissolved 33.4 mg (0.0728 mmol) of4,6-dichloro-3-[2,4-dibromo-5-(ethylsulfanyl)phenoxy]pyridazine obtainedin (1), 29.8 mg (0.363 mmol) of sodium acetate was added to the solutionand the resulting mixture was stirred at 120° C. for 4 hours and 30minutes. After allowing to stand at room temperature overnight, waterwas added to the reaction mixture, the mixture was made acidic by addingdiluted hydrochloric acid, and extracted with ethyl acetate. The organiclayers were combined, washed successively with water and brine. Afterdrying over anhydrous magnesium sulfate, the solvent was distilled offand the obtained residue was purified by preparative thin-layerchromatography (available from MERCK Co., 1.05744, developed multiply byethyl acetate) to obtain 13.1 mg (0.0297 mmol, Yield: 40.8%) of6-chloro-3-[2,4-dibromo-5-(ethylsulfanyl)phenoxy]-4-pyridazinol(Compound No. 2596).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.84 (1H, s), 7.21 (1H, s) 6.72 (1H, s),2.97 (2H, q, J=7.3 Hz), 1.33 (3H, t, J=7.3 Hz). Melting point (° C.):225-228.

EXAMPLE 633 6-Chloro-3-(2,3,5-trimethyl-6-vinylphenoxy)-4-pyridazinol(Compound No. 2603) (1) 1-(2-Methoxy-3,4,6-trimethylphenyl)ethanone

In acetone (30 mL) was dissolved 2.00 g (11.2 mmol) of1-(2-hydroxy-3,4,6-trimethylphenyl)ethanone which can be produced by themethod disclosed in Chemical Research in Toxicology, 1997, vol. 10, No.3, pp. 335-343, 3.10 g (22.4 mmol) of potassium carbonate, then 1.40 mL(22.5 mmol) of methyl iodide were added to the solution, and theresulting mixture was refluxed for 5 hours. After cooling to roomtemperature, the reaction mixture was concentrated, and the residue waspoured into water, and extracted with ethyl acetate. The organic layerswere combined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (Wako gel C-100,hexane:ethyl acetate gradient) to obtain 1.90 g (9.90 mmol, Yield:88.4%) of 1-(2-methoxy-3,4,6-trimethylphenyl)ethanone.

(2) 1-(2-Methoxy-3,4,6-trimethylphenyl)ethanol

In methanol (8 mL) was dissolved 1.00 g (5.21 mmol) of1-(2-methoxy-3,4,6-trimethylphenyl)ethanone obtained in (1), and 170 mg(4.50 mmol) of sodium borohydride was added to the solution little bylittle with stirring. After confirmation of disappearance of thestarting materials by thin layer chromatography (TLC) for analysis, thereaction mixture was poured into water, and made acidic by addinghydrochloric acid. The mixture was extracted with hexane, the organiclayers were combined, washed successively with water and brine, anddried over anhydrous magnesium sulfate. The solvent was removed toobtain 1.0 g of 1-(2-methoxy-3,4,6-trimethylphenyl)ethanol.

(3) 2-(l-Chloroethyl)-3-methoxy-1,4,5-trimethylbenzene

In dichloromethane(10 mL) was dissolved 1.0 g of1-(2-methoxy-3,4,6-trimethylphenyl)ethanol obtained in (2), and 1.10 mL(7.91 mmol) of triethylamine, then, 0.56 mL (7.21 mmol) ofmethanesulfonyl chloride were added to the solution in an ice bath withstirring. The reaction mixture was stirred at room temperature for 20minutes, poured into water, and extracted with dichloromethane. Theorganic layers were combined, washed successively with water and brine,and dried over anhydrous magnesium sulfate. The solvent was removed toobtain 1.2 g of 2-(1-chloroethyl)-3-methoxy-1,4,5-trimethylbenzene.

(4) 3-Methoxy-1,2,5-trimethyl-4-vinylbenzene

In dry N,N-dimethylformamide (12 mL) was dissolved 1.2 g of2-(1-chloroethyl)-3-methoxy-1,4,5-trimethylbenzene obtained in (3), and1.14 g (10.2 mmol) of potassium tertbutoxide was added to the solutionin an ice bath with stirring. The reaction mixture was stirred at roomtemperature for 30 minutes, then, under reflux for 30 minutes. Aftercooling to room temperature, the mixture was poured into water, andextracted with hexane. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was removed to obtain 870 mg of3-methoxy-1,2,5-trimethyl-4-vinylbenzene.

(5) 2,3,5-Trimethyl-6-vinylphenol and2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenol

Under nitrogen atmosphere, in dry N,N-dimethylformamide (8 mL) wassuspended 270 mg (6.75 mmol) of 60% sodium hydride, and 0.60 mL (8.10mmol) of ethanethiol was gradually added dropwise to the suspension.After stirring for 15 minutes, 400 mg (2.27 mmol) of3-methoxy-1,2,5-trimethyl-4-vinylbenzene obtained in (4) and dissolvedin dry N,N-dimethylformamide (1.5 mL) was added to the mixture, and theresulting mixture was refluxed for 1 hour. After cooling to roomtemperature, the reaction mixture was poured into water, made acidic byadding hydrochloric acid, and extracted with hexane. The organic layerswere combined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the residuewas purified by silica gel column chromatography (Wako gel C-100,hexane:ethyl acetate=20:1) and by preparative thin-layer chromatography(available from MERCK CO., 1.05744, developed by hexane:ethylacetate=8:1) to obtain 63.0 mg (0.389 mmol, Yield from1-(2-methoxy-3,4,6-trimethylphenyl)ethanone: 16.2%) of2,3,5-trimethyl-6-vinylphenol and 330 mg (1.47 mmol, Yield from1-(2-methoxy-3,4,6-trimethylphenyl)ethanone: 61.4%) of2-[1-(ethylsulfanylethyl]-3,5,6-trimethylphenol.

(6) Mixture of 6-chloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine1-oxide and 3-chloro-6-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine1-oxide (Step B-2)

In 1,4-dioxane (0.4 mL) and dimethylsulfoxide (0.4 mL) was dissolved43.0 mg (0.265 mmol) of 2,3,5-trimethyl-6-vinylphenol obtained in (5),36.0 mg (0.321 mmol) of potassium tert-butoxide was added to the mixturein an ice bath, and the resulting mixture was stirred for 10 minutes. Tothe mixture was added 47.6 mg (0.288 mmol) of 3,6-dichloropyridazine1-oxide in an ice bath, and the mixture was stirred at room temperaturefor 4 hours. The reaction mixture was poured into water, and extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was distilled off and the obtained residue waspurified by preparative thin-layer chromatography (available from MERCKCO., 1.05744, 2 plates were used, developed by hexane:ethyl acetate=2:1)to obtain 27.6 mg (0.0949 mmol, Yield: 35.8%) of a mixture of6-chloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine 1-oxide and3-chloro-6-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine 1-oxide.

(7) 4,6-Dichloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine (Step B-3)

0.02 mL (0.22 mmol) of phosphorus oxychloride was added to 27.6 mg(0.0949 mmol) of a mixture of6-chloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine 1-oxide and3-chloro-6-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine 1-oxide obtainedin (6), and the resulting mixture was stirred at room temperature for 2hours. To the mixture was added 0.4 mL of chloroform, and the resultingmixture was stirred at room temperature overnight. The reaction mixturewas concentrated, 0.2 mL (2.2 mmol) of phosphorus oxychloride was addedto the residue and the resulting mixture was stirred at room temperaturefor 5 hours. The reaction mixture was concentrated, the residue waspurified by preparative thin-layer chromatography (available from MERCKCO., 1.05744, 1 plate was used, developed by hexane:ethyl acetate=5:1)to obtain 5.0 mg (0.016 mmol, Yield: 17%) of4,6-dichloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine.

(8) 6-Chloro-3-(2,3,5-trimethyl-6-vinylphenoxy)-4-pyridazinol (CompoundNo. 2603, Step A-3 and Step A-4)

In dimethylsulfoxide(1 mL) was dissolved 5.0 mg (0.016 mmol) of4,6-dichloro-3-(2,3,5-trimethyl-6-vinylphenoxy)pyridazine obtained in(7), 10.3 mg (0.126 mmol) of sodium acetate was added to the solutionand the resulting mixture was stirred at 120° C. for 2 hours. Aftercooling to room temperature, the reaction mixture was poured into water,made acidic by adding hydrochloric acid, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine. After drying over anhydrous magnesium sulfate, thesolvent was distilled off and the obtained residue was purified bypreparative thin-layer chromatography (available from MERCK CO.,1.05744, 1 plate was used, developed by ethyl acetate) to obtain 1.5 mg(0.0052 mmol, Yield: 33%) of6-chloro-3-(2,3,5-trimethyl-6-vinylphenoxy)-4-pyridazinol (Compound No.2603).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.25 (1H, s), 6.67 (1H, dd, J=11.0 Hz,17.6 Hz), 6.56 (1H, s), 5.66 (1H, dd, J=1.5 Hz, 17.6 Hz), 5.10 (1H, dd,J=1.5 Hz, 11.0 Hz), 2.29 (3H, s), 2.20 (3H, s), 2.04 (3H, s).Appearance: amorphous.

EXAMPLE 6346-Chloro-3-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-pyridazinol(Compound No. 2606) (1)6-Chloro-3-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-methoxypyridazine(StepD-1)

In a mixed solvent of 1,4-dioxane (2 mL) and dimethylsulfoxide (2 mL)was dissolved 150 mg (0.670 mmol) of2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenol obtained in Example633(5), 93 mg (0.83 mmol) of potassium tert-butoxide was added to thesolution in an ice bath, and the resulting mixture was stirred at roomtemperature for 20 minutes. The mixture was again cooled in an ice bath,120 mg (0.670 mmol) of 3,6-dichloro-4-methoxypyridazine was added to themixture, and the resulting mixture was stirred at room temperatureovernight. The reaction mixture was poured into water, and extractedwith ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel chromatography (Wakogel C-100, hexane-ethyl acetate,gradient) and by preparative thin-layer chromatography (available fromMERCK CO., 1.05744, 2 plates were used, developed by hexane:ethylacetate=2:1) to obtain 26.7 mg (0.0728 mmol, Yield: 10.9%) of6-chloro-3-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-methoxypyridazine.Also, 60.0 mg (0.163 mmol, Yield: 24.3%) of3-chloro-6-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-methoxypyridazinewas obtained.

(2)6-Chloro-3-{2-[l-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-pyridazinol(Compound No. 2606, Step D-2)

In dimethylsulfoxide (1 mL) was dissolved 34.0 mg (0.358 mmol) of2-hydroxypyridine, 41.0 mg (0.366 mmol) of potassium tert-butoxide wasadded to the solution at room temperature, and the resulting mixture wasstirred at room temperature for 20 minutes. To the mixture was added adimethylsulfoxide (1 mL) solution containing 26.7 mg (0.0728 mmol) of6-chloro-3-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-methoxypyridazineobtained in (1), and the resulting mixture was stirred at 60° C. Aftercompletion of the reaction, the reaction mixture was allowed to standfor cooling, and poured into water. After making the mixture acidic byadding hydrochloric acid to the mixture, and the mixture was extractedwith ethyl acetate. The organic layers were combined, and washedsuccessively with water and brine. After drying over anhydrous magnesiumsulfate, the solvent was removed. The obtained residue was purified bypreparative thin-layer chromatography (available from Merck Co.,1.05744, developed by ethyl acetate) to obtain 6.6 mg (0.019 mmol,Yield: 26%) of6-chloro-3-{2-[1-(ethylsulfanyl)ethyl]-3,5,6-trimethylphenoxy}-4-pyridazinol(Compound No. 2606).

¹H-NMR (200 MHz, CD₃OD) 8 ppm: 7.20 (2H, s), 6.64 (1H, s), 2.40-2.15(8H, m), 2.03 (3H, s), 1.40 (3H, d, J=7.0 Hz), 1.24 (1H, m), 1.03 (3H,t, J=7.3 Hz). Appearance: amorphous.

EXAMPLE 635 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl phthalate (CompoundNo. 1625) andbis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl] phthalate(Compound No. 2838, Step I)

In acetonitrile (3 mL) was suspended 207 mg (0.726 mmol) of(2,4-dichlorophenyl)(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)methanone,81.6 mg (0.729 mmol) of 1,4-diazabicyclo[2.2.2]octane was added to thesuspension and the resulting mixture was stirred. To the mixture wasadded 105

L (0.729 mmol) of phthaloyl dichloride, and after stirring at roomtemperature for 1 hour, 200 mg (0.722 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was furtheradded, and the resulting mixture was stirred at room temperature for 1hour and 30 minutes. The reaction mixture was poured into ice-water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous sodiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (Daisogel 1001W, hexane:ethylacetate, gradient) to obtain 28.0 mg (0.0405 mmol, Yield: 5.61%) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl phthalate (CompoundNo. 1625) and 163 mg (0.238 mmol, Yield: 33.0%) ofbis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl] phthalate(Compound No. 2838).

6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl phthalate (CompoundNo. 1625):

¹H-NMR (200 MHz, CDCl₃) 8 ppm: 8.01-7.96 (1H, m), 7.89-7.68 (3H, m),7.57 (1H, s), 7.29-7.06 (5H, m), 6.90-6.83 (1H, m), 3.71 (3H, s), 2.27(3H, s), 2.13 (3H, s), 1.82-1.68 (1H, m), 0.77-0.53 (4H, m). Appearance:amorphous.

Bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl] phthalate(Compound No. 2838):

¹H-NMR (200 MHz, CDCl₃) 8 ppm: 8.13-8.06 (2H, m), 7.84-7.78 (2H, m),7.58 (2H, s), 7.15-7.06 (4H, m), 6.90-6.83 (2H, m), 2.13 (6H, s),1.82-1.68 (2H, m), 0.73-0.52 (8H, m). Appearance: amorphous.

EXAMPLE 636 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl1,3-benzenedisulfonate (Compound No. 2333) andbis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]1,3-benzenedisulfonate (Compound No. 3755, Step I)

In acetonitrile (4 mL) was suspended 122 mg (0.428 mmol) of(2,4-dichlorophenyl)(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)methanone,72.0 mg (0.643 mmol) of 1,4-diazabicyclo[2.2.2]octane, then 117 mg(0.425 mmol) of 1,3-benzenedisulfonyl dichloride were added to thesuspension in an ice bath, and the resulting mixture was stirred at roomtemperature for 30 minutes. The reaction mixture was ice-cooled, andfurther 100 mg (0.361 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was added tothe mixture, and the mixture was stirred at room temperature for 1 hour.The reaction mixture was poured into water, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, and dried over anhydrous magnesium sulfate. The solventwas removed, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane:ethyl acetate, gradient) toobtain 135 mg (0.177 mmol, Yield: 49.0%) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl1,3-benzenedisulfonate (Compound No. 2333) and 38.0 mg (0.0503 mmol,Yield: 13.9%) ofbis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]1,3-benzenedisulfonate (Compound No. 3755).

6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl1,3-benzenedisulfonate (Compound No. 2333):

H-NMR (200 MHz, CDCl₃) δ ppm: 8.67 (1H, t, J=1.9 Hz), 8.40-8.34 (1H, m),8.31-8.24 (1H, m), 7.86 (1H, t, J=8.0 Hz), 7.56 (1H, s), 7.37 (1H, d,J=1.9 Hz), 7.29-7.23 (1H, m), 7.15-7.00 (3H, m), 6.85-6.78 (1H, m), 3.81(3H, s), 2.00 (3H, s), 1.94 (3H, s), 1.70-1.52 (1H, m), 0.73-0.45 (4H,m). Appearance: amorphous.

Bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]1,3-benzenedisulfonate (Compound No. 3755):

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.77 (1H, dd, J=1.8 Hz, 1.8 Hz), 8.41(2H, dd, J=7.7 Hz, 1.8 Hz), 7.88 (1H, t, J=8.0 Hz), 7.48 (2H, s),7.15-6.95 (4H, m), 6.90-6.75 (2H, m), 1.97 (6H, s), 1.67-1.46 (2H, m),0.75-0.44 (8H, m). Appearance: amorphous.

EXAMPLE 637Bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]pentanedioate (Compound No. 2746) and6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl pentanedioate(Compound No. 2739)

In acetonitrile (8 mL) was suspended 241 mg (0.870 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, in an ice bath139 mg (1.23 mmol) of 1,4-diazabicyclo[2.2.2]octane, then 146 mg (0.864mmol) of pentanedioyl dichloride, and further 244 mg (0.856 mmol) of(2,4-dichlorophenyl)(5-hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)methanonewere added to the suspension, and the resulting mixture was stirred atroom temperature. The reaction mixture was poured into water, andextracted with ethyl acetate. The organic layers were combined, washedsuccessively with water and brine, and dried over anhydrous magnesiumsulfate. The solvent was removed, and the obtained residue was purifiedby silica gel column chromatography (Wako gel C-100, hexane: ethylacetate, gradient) and by preparative thin-layer chromatography(available from MERCK CO., 1.05744, 2 plates were used, developed byhexane:ethyl acetate=2:1 or 1:1) to obtain 42.0 mg (0.0646 mmol, Yield:7.48%) of bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]pentanedioate (Compound No. 2746) and 35.0 mg (0.0532 mmol, Yield:6.21%) of 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl pentanedioate(Compound No. 2739).

Bis[6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl]pentanedioate (Compound No. 2746):

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.23 (2H, s), 7.14-7.02 (4H, m), 6.83(2H, dd, J=6.6, 2.9 Hz), 2.89 (4H, t, J=7.0 Hz), 2.25 (2H, quintet,J=7.0 Hz), 2.10 (6H, s), 1.80-1.65 (2H, m), 0.78-0.52 (8H, m).Appearance: caramel-like.

6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yl pentanedioate(Compound No. 2739):

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.45-7.17 (4H, m), 7.14-7.00 (2H, m),6.90-6.75 (1H, m), 3.53 (3H, s), 2.83 (2H, t, J=7.0 Hz), 2.57 (2H, t,J=7.0 Hz), 2.20-2.00 (2H, m), 2.11 (3H, s), 2.10 (3H, s), 1.80-1.65 (1H,m), 0.80-0.50 (4H, m). Appearance: amorphous.

EXAMPLE 638 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-pyrrolidinecarboxylate (Compound No. 1937)

200 mg (0.722 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was mixed withtoluene (3 mL) and the mixture was ice-cooled. To the mixture were added60

L (0.742 mmol) of pyridine, then 0.67 mL (0.724 mmol) of 1.08 mol/Lphosgene-toluene solution under nitrogen atmosphere with stirring, andthe resulting mixture was stirred at room temperature for 15 minutes.The reaction mixture was ice-cooled, 60

L (0.722 mmol) of pyridine, then 60

L (0.719 mmol) of pyrrolidine were added to the mixture, and theresulting mixture was stirred at room temperature for 1 hour. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, and dried over anhydrous magnesium sulfate. The solventwas distilled off and the obtained residue was purified by preparativethin-layer chromatography (available from MERCK CO., 1.05744, 4 plateswere used, developed by hexane:ethyl acetate=2:1) to obtain 190 mg(0.508 mmol, Yield: 70.7%) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-pyrrolidinecarboxylate (Compound No. 1937).

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.59 (1H, s), 7.15-7.03 (2H, m),6.90-6.80 (1H, m), 3.62 (2H, dd, J=6.6 Hz, 6.9 Hz), 3.51 (2H, dd, J=6.9Hz, 6.6 Hz), 2.15 (3H, s), 2.05-1.90 (4H, m), 1.88-1.68 (1H, m),0.80-0.50 (4H, m). Melting point (° C.): 115-118.

EXAMPLE 639 6-Chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethoxy(methyl)carbamate (Compound No. 3564)

200 mg (0.722 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol was mixed withtoluene (3 mL) and the mixture was ice-cooled. To the mixture were added60

L (0.742 mmol) of pyridine, then 0.67 mL (0.724 mmol) of 1.08 mol/Lphosgene-toluene solution under nitrogen atmosphere with stirring, andthe resulting mixture was stirred at room temperature for 15 minutes.The reaction mixture was ice-cooled, 120

L (1.48 mmol) of pyridine, then 70.4 mg (0.722 mmol) ofN,O-dimethylhydroxylamine hydrochloride were added to the mixture, andthe resulting mixture was stirred at room temperature for 1 hour. Thereaction mixture was poured into water, and extracted with ethylacetate. The organic layers were combined, washed successively withwater and brine, and dried over anhydrous magnesium sulfate. The solventwas removed, and the obtained residue was purified by silica gel columnchromatography (Wako gel C-100, hexane: ethyl acetate, gradient) toobtain 100 mg (0.275 mmol, Yield: 38.1%) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylmethoxy(methyl)carbamate (Compound No. 3564).

¹H-NMR (200 MHz, CDCl₃) δ ppm: 7.53 (1H, s), 7.15-7.03 (2H, m),6.90-6.82 (1H, m), 3.84 (3H, s), 3.35 (3H, s), 2.15 (3H, s), 1.87-1.67(1H, m), 0.80-0.52 (4H, m). Melting point (° C.): 63-64.5.

EXAMPLE 640 6-Chloro-3-(2-cyclopropyl-6-methylphen6xy)-4-pyridazinyl2,5-dimethyl-1H-pyrrole-1-carboxylate (Compound No. 3630)

37.4 mg (0.393 mmol) of 2,5-dimethyl-1H-pyrrole was mixed with toluene(1 mL), 40.0

L (0.407 mmol) of pyridine, then 0.34 mL (0.367 mmol) of 1.08 mol/Lphosgene-toluene solution were added to the mixture in an ice bath withstirring, and the resulting mixture was stirred for 1 hour. To themixture were added 40.0

L (0.407 mmol) of pyridine, then 100 mg (0.361 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and theresulting mixture was stirred for 3 hours. The reaction mixture waspoured into water, and extracted with ethyl acetate. The organic layerswere combined, washed with water, and dried over anhydrous magnesiumsulfate. The solvent was distilled off and the obtained residue waspurified by preparative thin-layer chromatography (available from MERCKCO., 1.05744, 2 plates were used, developed by hexane:ethyl acetate=2:1)to obtain 24.0 mg (0.0603 mmol, Yield: 16.7%) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl2,5-dimethyl-1H-pyrrole-1-carboxylate (Compound No. 3630).

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.20-8.03 (1H, m), 7.63 (1H, s),7.13-7.00 (2H, m), 6.90-6.80 (1H, m), 6.36 (1H, d, J=2.9 Hz), 2.55 (3H,s), 2.22 (3H, s), 2.15 (3H, s), 1.90-1.70 (1H, m), 0.80-0.50 (4H, m).Melting point (° C.): 208-210.

EXAMPLE 6414-{[4-(benzoyloxy)-6-chloro-3-pyridazinyl]oxy}-3-methylphenyl benzoate(Compound No. 3850) (1)6-Chloro-3-(4-hydroxy-2-methylphenoxy)-4-pyridazinol

In 1,4-dioxane(1.4 mL) was dissolved 173 mg (0.553 mmol) of4-[(4,6-dichloro-3-pyridazinyl)oxy]-3-methylphenyl acetate obtained inExample 630(3), 0.7 mL (2.1 mmol) of 3 mol/L sodium hydroxide solutionand dimethylsulfoxide (2.8 mL) were added to the solution and theresulting mixture was stirred at room temperature overnight. To thereaction mixture was added 4 mol/L hydrochloric acid, and the mixturewas extracted with ethyl acetate. The organic layers were combined,washed successively with water and brine. After drying over anhydrousmagnesium sulfate, the solvent was removed. The obtained residue waspurified by preparative thin-layer chromatography (developed bydichloromethane:methanol=36:1) to obtain 66.8 mg of6-chloro-3-(4-hydroxy-2-methylphenoxy)-4-pyridazinol.

(2) 4-{[4-(Benzoyloxy)-6-chloro-3-pyridazinyl]oxy}-3-methylphenylbenzoate (Compound No. 3850)

In acetonitrile (1.0 mL) was dissolved 66.8 mg of6-chloro-3-(4-hydroxy-2-methylphenoxy)-4-pyridazinol obtained in (1),60.0 mg (0.536 mmol) of 1,4-diazabicyclo[2.2.2]-octane, then, 61

L (0.523 mmol) of benzoyl chloride were added to the solution and theresulting mixture was stirred at room temperature for 1 hour and 30minutes. The reaction mixture was poured into water, and extracted withethyl acetate. The organic layers were combined, washed successivelywith water and brine. After drying over anhydrous magnesium sulfate, thesolvent was removed. The obtained residue was purified by preparativethin-layer chromatography (developed by hexane:ethyl acetate=5:1) toobtain 36.9 mg (0.0800 mmol, Yield from4-[(4,6-dichloro-3-pyridazinyl)oxy]-3-methylphenyl acetate: 14.5%) of4-{[4-(benzoyloxy)-6-chloro-3-pyridazinyl]oxy}-3-methylphenyl benzoate(Compound No. 3850).

¹H-NMR (200 MHz, CDCl₃) δ ppm: 8.21-8.17 (4H, m), 7.72-7.48 (7H, m),7.22-7.07 (3H, m), 2.21 (3H, s). Melting point (° C.): 118-120.

EXAMPLE 642 3-(2-Aminophenoxy)-3-chloro-4-pyridazinol (Compound No. 377)(1) 2-[(6-chloro-4-methoxy-3-pyridazinyl)oxy]aniline(Step D-1)

In a mixed solvent of 1,4-dioxane (7 mL) and dimethylsulfoxide (7 mL)was dissolved 670 mg (6.15 mmol) of 2-aminophenol, 690 mg (6.16 mmol) ofpotassium tertbutoxide was added to the solution in an ice bath and theresulting mixture was stirred for 10 minutes. To the mixture was added1000 mg (5.59 mmol) of 3,6-dichloro-4-methoxypyridazine, and theresulting mixture was stirred at room temperature for 5 hours. Thereaction mixture was poured into ice water, and after adding brine, themixture was extracted with ethyl acetate. The organic layers werecombined, washed successively with water and brine, and dried overanhydrous magnesium sulfate. The solvent was removed, and the obtainedresidue was purified by silica gel chromatography (Wakogel C-100,hexane-ethyl acetate, gradient) to obtain 328 mg (1.30 mmol, Yield:23.3%) of 2-[(6-chloro-4-methoxy-3-pyridazinyl)oxy]aniline and 100 mg ofa mixture of 2-[(6-chloro-4-methoxy-3-pyridazinyl)oxy]aniline and2-[(6-chloro-5-methoxy-3-pyridazinyl)oxy]aniline.

(2) 3-(2-Aminophenoxy)-3-chloro-4-pyridazinol (Compound No. 377, StepD-2)

In dimethylsulfoxide (0.4 mL) was dissolved 50.0 mg (0.198 mmol) of2-[(6-chloro-4-methoxy-3-pyridazinyl)oxy]aniline obtained in (1), (0.2mL, 0.4 mmol) of 2 mol/L aqueous sodium hydroxide solution was added tothe solution and the resulting mixture was stirred at room temperaturefor 5 hours. The reaction mixture was poured into brine, and extractedwith tetrahydrofuran. The organic layers were combined, washed withbrineand dried over anhydrous magnesium sulfate. The solvent wasdistilled off and the residue was purified by preparative thin-layerchromatography (available from MERCK CO., 1.05744, 2 plates were used,developed by dichloromethane:methanol=10:1) to obtain 17.0 mg (0.0714mmol, Yield: 36.1%) of 3-(2-aminophenoxy)-3-chloro-4-pyridazinol(Compound No. 377).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.50-6.94 (2H, m), 6.90-6.82 (1H, m),6.85-6.63 (2H, m). Melting point (° C.): 249-250.

EXAMPLE 643 N-{2-[(6-Chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}acetamide(Compound No. 380)

18.0 mg (0.0756 mmol) of 3-(2-aminophenoxy)-3-chloro-4-pyridazinolobtained in Example 641 was mixed with dichloromethane (0.8 mL), 0.050mL (0.36 mmol) of triethylamine, then 0.010 mL (0.14 mmol) of acetylchloride were added to the mixture in an ice bath with stirring, and theresulting mixture was stirred at room temperature for 3 hours. Thereaction mixture was poured into brine, and extracted withtetrahydrofuran. The organic layers were combined, washed with brineanddried over anhydrous magnesium sulfate. The solvent was distilled offand the residue was purified by preparative thin-layer chromatography(available from MERCK CO., 1.05715, developed bydichloromethane:methanol=10:1) to obtain 3.6 mg (0.0129 mmol, Yield:17.1%) of N-{2-[(6-chloro-4-hydroxy-3-pyridazinyl)oxy]phenyl}acetamide(Compound No. 380).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 8.10-8.00 (1H, m), 7.25-7.08 (3H, m),6.60 (1H, s), 2.12 (3H, s). Melting point (° C.): 135.

EXAMPLE 644 N,N,N-Tributyl-1-butanaminium6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinolate(Compound No.3798)

To an ethanol (2 mL) solution containing 105 mg (0.379 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol were added 0.19mL (0.38 mmol) of 2 mol/L aqueous sodium hydroxide solution, then, 106mg (0.381 mmol) of tetrabutylammonium chloride, and the resultingmixture was stirred at 60° C. for 5 hours. The reaction mixture wasallowed to stand at room temperature overnight, and the solid wasremoved by filtration. The filtrate was concentrated to obtainN,N,N-tributyl-1-butanaminium6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinolate (CompoundNo. 3798).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.05-6.95 (2H, m), 6.80-6.73 (1H, m),6.43 (1H, s), 3.30-3.15 (8H, m), 2.14 (3H, s), 2.00-1.85 (1H, m),1.76-1.53 (8H, m), 1.50-1.30 (8H, m), 1.02 (9H, t, J=7.1 Hz), 0.78-0.63(2H, m), 0.63-0.48 (2H, m). Melting point (° C.): 113-114.

EXAMPLE 645 Sodium6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinolate (CompoundNo. 3805)

0.18 mL (0.36 mmol) of 2 mol/L aqueous sodium hydroxide solution wasadded to an ethanol (2 mL) solution containing 100 mg (0.361 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and theresulting mixture was stirred at 50° C. for 4 hours. The reactionmixture was concentrated to obtain 108 mg (0.361 mmol, Yield: 100%) ofsodium 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinolate(Compound No. 3805).

¹H-NMR (200 MHz, CD₃OD) 8 ppm: 7.05-6.95 (2H, m), 6.77 (1H, dd,J=6.4,3.1 Hz), 6.43 (1H, s), 2.14 (3H, s), 2.00-1.82 (1H, m), 0.78-0.63 (2H,m), 0.63-0.48 (2H, m). Melting point (° C.): >260.

EXAMPLE 6465-Bromo-6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol(Compound No. 3843)

108 mg (0.607 mmol) of N-bromosuccinimide was added to aN,N-dimethylformamide (2 mL) solution containing 157 mg (0.567 mmol) of6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol, and theresulting mixture was stirred at room temperature for 3 hours and 30minutes. Water, and then, 4 mol/L hydrochloric acid were added to thereaction mixture, and the mixture was extracted with ethyl acetate. Theorganic layers were combined, washed successively with water and brine,and dried over anhydrous magnesium sulfate. The solvent was distilledoff and the residue was purified by preparative thin-layerchromatography (available from MERCK CO. 1.05744, developed byhexane:ethyl acetate=2:1) to obtain 123 mg (0.346 mmol, Yield: 61.0%) of5-bromo-6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol(Compound No. 3843).

¹H-NMR (200 MHz, CD₃OD) δ ppm: 7.08-7.05 (2H, m), 6.85-6.80 (1H, m),2.14 (3H, s), 1.88-1.76 (1H, m), 0.82-0.72 (2H, m), 0.60-0.56 (2H, m).Appearance: amorphous.

Compounds of Compounds Nos. 1 and 6 can be produced in accordance withthe method of Example 2.

Compounds of Compounds Nos. 123-127, 130-138, 144, 145, 151, 163, 173,184, 202, 217, 226, 249, 264, 265, 266, 267, 269-275, 279, 280, 284,287, 288, 292, 293, 300, 304, 305, 306, 307, 308, 309, 311, 315, 324,325, 329, 330, 334, 336, 339, 344, 348, 349, 355, 356, 359, 361, 362,364-370, 375, 376, 379, 383, 385-387, 390, 391, 396, 399-401, 403, 410,412, 413, 415-425, 426, 427, 430, 432-438, 441, 443, 446, 450, 453, 454,456, 458-460, 472, 491, 498, 503, 505, 506, 507, 510, 513, 514, 520,521, 527-529, 531, 532, 534-536, 538-541, 544, 547, 549, 552, 556, 557,558, 559, 562, 566, 567, 571, 614, 618, 621, 623, 626-629, 635, 640,642, 650, 653, 658, 659, 662-664, 667, 679, 680, 692, 700, 701, 702,707-712, 716, 71.7, 719, 731-733, 734, 735-737, 740, 746, 754, 756, 758,759, 762, 775, 778, 780-782, 802-804, 834, 844-846, 850, 890, 894, 896,911, 914, 931, 964, 965, 979, 982, 987, 998, 1000, 1007, 1009, 1013,1016, 1020, 1023, 1027, 1040, 1050, 1052, 1053, 1055, 1058, 1060, 1061,1063, 1064, 1066, 1069, 1073, 1080, 1083, 1086, 1088, 1089, 1091, 1096,1099, 1100, 1102, 1115, 1118-1120, 1122-1125, 1129, 1133, 2519, 2547,2548, 2565, 2568, 2570, 2571, 2574, 2577, 2585, 2587, 2589, 2592, 2597,2599, 2600, 2601, 2605, 2607, 2608, 2609 and 2614 can be produced inaccordance with the method of Example 1, Example 6, Example 13, Example16, Example 21, Example 22 or Example 23.

Compounds of Compound No. 1140, 1151, 1160, 1172, 1178, 1184, 1207,1251, 1260, 1266, 1286, 1298, 1334, 1340, 1358, 1364, 1382, 1387, 1391,1396, 1417, 1441, 1446, 1448, 1450, 1455-1459, 1461, 1481, 1509, 1522,1531, 1537, 1543, 1549, 1553, 1554, 1566, 1575, 1593, 1599, 1603, 1616,1643, 1649, 1658, 1706, 1710, 1757, 1770, 1789, 1811, 1840, 1877, 1879,1881, 1898, 1924, 1981, 1985, 2010, 2034, 2038, 2040, 2042, 2051, 2060,2066, 2072, 2106, 2136, 2147, 2151, 2176, 2198-2200, 2212, 2220-2224,2230-2232, 2234-2238, 2240, 2245-2249, 2263, 2265, 2287, 2289, 2300,2309, 2315, 2321, 2351, 2662, 2671, 2677, 2697, 2703, 2709, 2715, 2721,2727, 2752, 2758, 2764, 2770, 2776, 2782, 2788, 2805, 2814, 2820, 2826,2850, 2856, 2862, 2868, 2874, 2880, 2900, 2906, 2918, 2924, 2930, 2961,2970, 2976, 2982, 2988, 2994, 3016, 3022, 3028, 3034, 3040, 3046, 3052,3058, 3064, 3070, 3076, 3082, 3088, 3094, 3100, 3106, 3112, 3129, 3138,3144, 3150, 3156, 3162, 3168, 3185, 3194, 3200, 3217, 3226, 3243, 3252,3258, 3264, 3270, 3276, 3282, 3288, 3294, 3300, 3306, 3312, 3318, 3324,3330, 3336, 3342, 3348, 3354, 3360, 3366, 3372, 3378, 3384, 3390, 3396,3402, 3408, 3414, 3420, 3426, 3432, 3438, 3444, 3450, 3456, 3462, 3468,3474, 3480, 3486, 3492, 3498, 3504, 3510, 3516, 3780, 3786, 3792 and3856 can be produced in accordance with the method of Example 26,Example 27 or Example 28.

A compound of Compound No. 2402 can be produced in accordance with themethod of Example 33.

Compounds of Compound No. 2418 and 2431 can be produced in accordancewith the method of Example 1, Example 6 or Example 22.

A compound of Compound No. 2478 can be produced in accordance with themethod of Example 35, Example 36, Example 37, Example 39 or Example 40.

A compound of Compound No. 2492 can be produced in accordance with themethod of Example 41.

Compounds of Compound No. 1620, 1631, 2827 and 3001 can be produced inaccordance with the method of Example 635.

Compounds of Compound No. 1891, 1911, 1920, 1946, 1952, 1958, 3522,3528, 3534, 3540, 3546, 35.52, 3558, 3570, 3576, 3582, 3588, 3594, 3600,3606, 3612, 3618, 3624, 3636, 3642, 3648, 3654, 3660, 3666, 3672, 3678,3684, 3690, 3696, 3702, 3708, 3714 and 3720 can be produced inaccordance with the method of Example 26, Example 27, Example 28,Example 638, Example 639 or Example 640.

A compound of Compound No. 2327 can be produced in accordance with themethod of Example 636.

A compound of Compound No. 2733 can be produced in accordance with themethod of Example 637.

A compound of Compound No. 3811 can be produced in accordance with themethod of Example 645.

Compounds of Compound No. 3837 and 3849 can be produced in accordancewith the method of Example 646.

In the following Preparation example, all “%” mean % by weight.

PREPARATION EXAMPLE 1 Wettable Powder

A compound (10 parts by weight) of Example 1 (Compound No. 128), Carplex#80D (available from Shionogi & Co. Ltd., 10 parts by weight), GOHSENOLGL05 (available from The Nippon Synthetic Chemical Industry Co., Ltd., 2parts by weight), Newcol 291PG (dioctylsulfosuccinate sodium salt,available from Nippon Nyukazai Co., Ltd., 0.5 part by weight), NeogenPowder (available from DAI-ICHI KOGYO SEIYAKU CO., LTD., 5 parts byweight), Radiolite #200 (available from SHOWA CHEMICAL CO., LTD., 10parts by weight) and H Bifun (fine cray, available from Keiwa Rozai Co.,Ltd, 62.5 parts by weight) were sufficiently mixed, and pulverized byEcksample Mill Type KII-1 (available from Fuji Paudal Co., Ltd.) toobtain wettable powder.

PREPARATION EXAMPLE 2 Granule

A compound (5 parts by weight) of Example 61 (Compound No. 136), sodiumtripolyphosphate (available from Mitsui Chemicals, Inc., 2 parts byweight), Amycol No. 1 (dextrin, available from NIPPON STARCH CHEMICALCO., LTD., 1.5 parts by weight), bentonite (available from Hojun Co.,Ltd., 25 parts by weight) and Calfin 600 (calcium carbonate, availablefrom Ashidachi Sekkai K.K., 66.5 parts by weight) were mixed in akneader (available from Fujisangyo Co., Ltd., Type FM-NW-5), and water(13 parts by weight) was added to the mixture to carry out furthermixing, and subjected to extrusion granulation by using Dom Gran(available from Fuji Paudal Co., Ltd., screen 1.0 mmo). The obtainedgranules were dried by using a tray type dryer (available from TabaiK.K., PERFECT OVEN Type PS-222, 60° C.), and sieved to 600 to 1190 mm toobtain granules.

PREPARATION EXAMPLE 3 Water Dispersible Granules

A compound (80 parts by weight) of Example 7 (Compound No. 140), GeroponSC/213 (polycarboxylic acid type surfactant, available from Rohdia K.K.,7 parts by weight), Neopelex No. 6F Powder (dodecylbenzene sulfonate,KAO CORPORATION, 3 parts by weight), Amycol No. 1 (5 parts by weight)and titanium oxide (SAKAI CHEMICAL INDUSTRY CO., LTD., 5 parts byweight) are mixed, pulverized by air mill (SK-JET O MIZER model 0101,available from SEISHIN ENTERPRISE CO., LTD.,), then added to a rotarymixer, and granulated by spraying water. When almost all the part becomea size of 1.00 mm to 0.15 mm, then the granules are taken out, and afterdrying in a tray type dryer, they are sieved to obtain a granularwettable powder with a size of 1.00 mm to 0.15 mm.

PREPARATION EXAMPLE 4 Suspension Consentrato

A compound (10 parts by weight) of Example 171 (Compound No. 506),Newcol 291PG (1 parts by weight), Pearlrex CP (lignin sulfonic acidcalcium salt, available from NIPPON PAPER INDUSTRIES CO., LTD., 10 partsby weight), propylene glycol (available from Nippon Nyukazai Co., Ltd.,10 parts by weight) and water (69 parts by weight) were together mixedand pulverized in an attritor (MISUI MINING CO., LTD.) until thediameter of solid particles became 5 im or less. To the pulverizedslurry (90 parts by weight) was added 0.05% (W/W) xanthane gum aqueoussolution (10 parts by weight) and mixed to obtain an aqueous suspension.

PREPARATION EXAMPLE 5 Wettable Powder

A compound (10 parts by weight) of Example 6 (Compound No. 139),Compound A (10 parts by weight), Carplex #80D (available from Shionogi &Co. Ltd., 10 parts by weight), GOHSENOL GL05-S (available from TheNippon Synthetic Chemical Industry Co., Ltd., 2 parts by weight), Newcol291PG (dioctylsulfosuccinate sodium salt, available from Nippon NyukazaiCo., Ltd., 0.5 parts by weight), Neogen Powder (available from DAI-ICHIKOGYO SEIYAKU CO., LTD., 5 parts by weight), Radiolite #200 (availablefrom SHOWA CHEMICAL CO., LTD., 10 parts by weight) and H Bifun (finecray, available from Keiwa Rozai Co., Ltd, 52.5 parts by weight) weresufficiently mixed. The mixture was pulverized by air mill (SK-JET OMIZER Model 0101, available from SEISHIN ENTERPRISE CO., LTD.,) toobtain mixed wettable powder of the compound (10%) of Example 6 andcompound A (10%).

PREPARATION EXAMPLE 6 Wettable Powder

A compound (10 parts by weight) of Example 23 (Compound No. 806),Compound B (10 parts by weight), Carplex #80D (available from Shionogi &Co. Ltd., 10 parts by weight), GOHSENOL GL05-S (available from TheNippon Synthetic Chemical Industry Co., Ltd., 2 parts by weight), Newcol291PG (dioctylsulfosuccinate sodium salt, available from Nippon NyukazaiCo., Ltd., 0.5 parts by weight), Neogen Powder (available from DAI-ICHIKOGYO SEIYAKU CO., LTD., 5 parts by weight), Radiolite #200 (availablefrom SHOWA CHEMICAL CO., LTD., 10 parts by weight) and H Bifun (finecray, available from Keiwa Rozai Co., Ltd, 52.5 parts by weight) weresufficiently mixed. The mixture was pulverized by air mill (SK-JET OMIZER Model 0101, available from SEISHIN ENTERPRISE CO., LTD.,) toobtain a mixed wettable powder of the compound (10%) of Example 23 andCompound B (10%).

PREPARATION EXAMPLE 7 Granules

Compound A (61.22 parts by weight), Newcol 291PG (0.85 parts by weight)and water (37.93 parts by weight) were mixed, and pulverized by using anattritor (available from MISUI MINING CO., LTD.) until the averageparticle size became about 2 im to obtain a slurry. To the slurry (98parts by weight) was added Toxanone (available from Sanyo ChemicalIndustries, Ltd., 2 parts by weight) and then mixed to obtain Slurry 2.A compound (5 parts by weight) of Example 171 (Compound No. 506), sodiumtripolyphosphate (available from Mitsui Chemicals, Inc., 2 parts byweight), Amycol No. 1 (dextrin, available from NIPPON STARCH CHEMICALCO., LTD., 1.5 parts by weight), bentonite (available from Hojun Co.,Ltd., 25 parts by weight) and Calfin 600 (calcium carbonate, availablefrom Ashidachi Sekkai K.K., 61.27 parts by weight) were mixed in akneader (available from Fujisangyo Co., Ltd., Type FM-NW-5), and furtherSlurry 2 (8.33 parts by weight) were added and mixed. The kneadingmaterial was subjected to extrusion granulation by using Dom Gran(available from Fuji Paudal Co., Ltd., screen 1.0 mmö), and the obtainedgranules were dried by using a tray type dryer (available from TabaiK.K., PERFECT OVEN Type PS-222, 60° C.), then sieved to a size of 600 to1190 mm to obtain granules of the compound. (5%) of Example 171 andCcompound A (5%).

PREPARATION EXAMPLE 8 Suspension Concentrato

A compound (11.11 parts by weight) of Example 1 (Compound No. 128),Compound C (11.11 parts by weight), Newcol 291PG (1 parts by weight),ligninsulfonic acid calcium salt (Pearlrex CP, available from NIPPONPAPER INDUSTRIES CO., LTD., 10 parts by weight), propylene glycol(available from Nippon Nyukazai Co., Ltd., 10 parts by weight) and water(56.78 parts by weight) were mixed and pulverized in an attritor (MISUIMINING CO., LTD.) until a diameter of solid particles became 5 im orless to obtain a slurry. To the slurry (90 parts) was added 0.05%xanthane gum aqueous solution (10 parts by weight) and mixed to obtain amixed aqueous suspension of the compound (10%) of Example 1 and CompoundC (10%).

PREPARATION EXAMPLE 9 Wettable Powder

A compound (10 parts by weight) of Example 23 (Compound No. 806),Compound D (2 parts by weight), Carplex #80D (available from Shionogi &Co. Ltd., 10 parts by weight), GOHSENOL GL05-S (available from TheNippon Synthetic Chemical Industry Co., Ltd., 2 parts by weight), Newcol291PG (dioctylsulfosuccinate sodium salt, available from Nippon NyukazaiCo., Ltd., 0.5 parts by weight), Neogen Powder (available from DAI-ICHIKOGYO SEIYAKU CO., LTD., 5 parts by weight), Radiolite #200 (availablefrom SHOWA CHEMICAL CO., LTD., 10 parts by weight) and H Bifun (finecray, available from Keiwa Rozai Co., Ltd, 60.5 parts by weight) weresufficiently mixed. The mixture was pulverized by air mill (SK-JET OMIZER Model 0101, available from SEISHIN ENTERPRISE CO., LTD.,) toobtain a mixed wettable powder of the compound (10%) of Example 23 andCompound D (2%).

PREPARATION EXAMPLE 10 Wettable Powder

A compound (10 parts by weight) of Example 23 (Compound No. 806),Compound E (8 parts by weight), Carplex #80D (available from Shionogi &Co. Ltd., 10 parts by weight), GOHSENOL GL05-S (available from TheNippon Synthetic Chemical Industry Co., Ltd., 2 parts by weight), Newcol291PG (dioctylsulfosuccinate sodium salt, available from Nippon NyukazaiCo., Ltd., 0.5 parts by weight), Neogen Powder (available from DAI-ICHIKOGYO SEIYAKU CO., LTD., 5 parts by weight), Radiolite #200 (availablefrom SHOWA CHEMICAL CO., LTD., 10 parts by weight) and H Bifun (finecray, available from Keiwa Rozai Co., Ltd, 54.5 parts by weight) weresufficiently mixed. The mixture was pulverized by air mill (SK-JET OMIZER Model 0101, available from SEISHIN ENTERPRISE CO., LTD.,) toobtain a mixed wettable powder of the compound (10%) of Example 23 andCompound E (8%).

PREPARATION EXAMPLE 11 Wettable Powder

In the same manner as in Preparation example 10 except for usingCompound F in place of Compound E, a mixed wettable powder of thecompound (10%) of Example 23 and Compound F (8%) was obtained.

TEST EXAMPLE 1 Tests of Herbicidal Effects and Crop Injury AgainstPaddy-field Rice

A paddy soil was filled in 1/10,000 are pot, and seeds of barnyardgrass(Echinochloa oryzicola Vasing.), Scirpus joncoides and annualbroad-leaved weeds (Lindernia spp., Rotala indica) which are awaken fromdormancy were mixed at the surface layer of 1 cm. Also, tuber of Cyperusserotinus which is germinated was planted, and further seedlings ofpaddy-field rice at 2.2-leaf stage were transplanted, and they weregrown under the flooded condition in a greenhouse. After 3 days fromtransplanting, a predetermined chemical dosage of the wettable powderprepared in accordance with Preparation example 1 was diluted in water,and the solution was applied to the pot and herbicidal effects and cropinjury against transplanted paddy-field rice were judged after 25 daysfrom the treatment. Also,3-(2-allylphenoxy)-6-chloro-4-methoxypyridazine described in ChemicalPharmaceutical Bulletin, 1972, vol. 20, No. 10, pp. 2191-2203 was usedas Comparative compound. The results are shown in Table 2. Incidentally,herbicidal effects and crop injury against transplanted paddy-field ricewere judged by the following judgment standard, and “-” in the tablemeans no test was carried out.

Judgment standard

-   0: Growth inhibition rate; 0 to 10%-   1: Growth inhibition rate; 11 to 30%-   2: Growth inhibition rate; 31 to 50%-   3: Growth inhibition rate; 51 to 70%-   5 4: Growth inhibition rate; 71 to 90%-   5: Growth inhibition rate; 91 to 100%.

TABLE 2 Crop injury against Chemical Herbicidal effects trans- dosageBarnyard Broad Scirpus Cyperus planted Test compound (g/a) grass leafjoncoides serotinus rice Compound of Example 1 25 5 5 5 5 0 (CompoundNo. 128) Compound of Example 1 12.5 4 5 5 5 0 (Compound No. 128)Compound of Example 6 20 3 5 5 5 0 (Compound No. 139) Compound ofExample 6 10 2 5 5 5 0 (Compound No. 139) Compound of Example 14 10 0 54 5 0 (Compound No. 515) Compound of Example 15 10 1 5 — 5 0 (CompoundNo. 516) Compound of Example 16 20 1 5 5 5 0 (Compound No. 704) Compoundof Example 16 10 0 5 5 5 0 (Compound No. 704) Compound of Example 18 251 5 4 5 2 (Compound No. 738) Compound of Example 18 12.5 0 5 3 5 1(Compound No. 738) Compound of Example 19 25 1 5 4 5 1 (Compound No.760) Compound of Example 19 12.5 0 5 4 5 1 (Compound No. 760) Compoundof Example 21 10 2 5 5 5 0 (Compound No. 801) Compound of Example 22 252 5 4 4 2 (Compound No. 805) Compound of Example 22 12.5 1 5 2 3 1(Compound No. 805) Compound of Example 23 20 4 5 5 5 2 (Compound No.806) Compound of Example 23 10 3 5 5 5 0 (Compound No. 806) Compound ofExample 26 20 4 5 5 5 0 (Compound No. 2081) Compound of Example 26 10 45 5 5 0 (Compound No. 2081) Compound of Example 27 20 4 5 5 5 0(Compound No. 2225) Compound of Example 27 10 2 5 4 5 0 (Compound No.2225) Compound of Example 34 20 2 4 4 5 0 (Compound No. 2411) Compoundof Example 34 10 1 2 2 5 0 (Compound No. 2411) Compound of Example 49 252 5 4 5 0 (Compound No. 124) Compound of Example 49 12.5 1 3 3 5 0(Compound No. 124) Compound of Example 50 25 3 5 4 5 0 (Compound No.125) Compound of Example 50 12.5 2 5 3 5 0 (Compound No. 125) Compoundof Example 51 25 2 5 5 5 0 (Compound No. 126) Compound of Example 5112.5 2 4 3 5 0 (Compound No. 126) Compound of Example 52 20 4 5 5 5 0(Compound No. 127) Compound of Example 52 10 3 5 5 5 0 (Compound No.127) Compound of Example 55 25 2 5 4 5 0 (Compound No. 130) Compound ofExample 55 12.5 2 5 3 5 0 (Compound No. 130) Compound of Example 56 25 05 3 4 0 (Compound No. 131) Compound of Example 56 12.5 0 4 2 4 0(Compound No. 131) Compound of Example 57 25 2 5 4 5 0 (Compound No.132) Compound of Example 57 12.5 2 5 3 5 0 (Compound No. 132) Compoundof Example 61 25 2 5 5 5 0 (Compound No. 136) Compound of Example 6112.5 1 5 5 5 0 (Compound No. 136) Compound of Example 72 20 3 5 5 5 0(Compound No. 217) Compound of Example 72 10 3 5 5 4 0 (Compound No.217) Compound of Example 85 10 2 4 3 5 0 (Compound No. 284) Compound ofExample 88 25 0 5 5 5 0 (Compound No. 292) Compound of Example 88 12.5 04 4 5 0 (Compound No. 292) Compound of Example 121 25 3 5 4 5 0(Compound No. 385) Compound of Example 121 12.5 2 5 3 5 0 (Compound No.385) Compound of Example 122 20 0 5 5 5 0 (Compound No. 386) Compound ofExample 122 10 0 5 4 5 0 (Compound No. 386) Compound of Example 123 20 15 4 5 0 (Compound No. 387) Compound of Example 123 10 0 5 3 4 0(Compound No. 387) Compound of Example 125 20 2 5 4 5 0 (Compound No.391) Compound of Example 125 10 1 5 3 4 0 (Compound No. 391) Compound ofExample 129 25 2 5 4 5 0 (Compound No. 401) Compound of Example 129 12.51 5 3 4 0 (Compound No. 401) Compound of Example 154 20 2 5 5 5 0(Compound No. 437) Compound of Example 154 10 1 5 3 5 0 (Compound No.437) Compound of Example 166 20 1 5 5 5 0 (Compound No. 472) Compound ofExample 166 10 0 5 5 5 0 (Compound No. 472) Compound of Example 171 20 45 5 5 0 (Compound No. 506) Compound of Example 171 10 3 5 5 5 0(Compound No. 506) Compound of Example 172 20 5 5 5 5 0 (Compound No.507) Compound of Example 172 10 5 5 5 4 0 (Compound No. 507) Compound ofExample 179 20 1 4 4 5 0 (Compound No. 521) Compound of Example 179 10 04 3 5 0 (Compound No. 521) Compound of Example 180 25 0 5 3 5 0(Compound No. 527) Compound of Example 180 12.5 0 5 2 5 0 (Compound No.527) Compound of Example 181 20 2 5 4 5 0 (Compound No. 528) Compound ofExample 181 10 1 5 3 4 0 (Compound No. 528) Compound of Example 182 20 25 4 5 0 (Compound No. 529) Compound of Example 183 20 2 5 5 5 0(Compound No. 531) Compound of Example 183 10 1 5 5 5 0 (Compound No.531) Compound of Example 184 20 0 5 4 5 0 (Compound No. 532) Compound ofExample 185 5 1 3 2 3 0 (Compound No. 534) Compound of Example 189 10 35 5 5 3 (Compound No. 539) Compound of Example 189 5 2 5 4 5 0 (CompoundNo. 539) Compound of Example 191 20 5 5 5 5 5 (Compound No. 541)Compound of Example 191 10 4 5 5 5 2 (Compound No. 541) Compound ofExample 192 20 5 3 5 5 1 (Compound No. 544) Compound of Example 192 10 22 5 5 0 (Compound No. 544) Compound of Example 202 10 2 5 — 4 0(Compound No. 571) Compound of Example 203 25 2 5 5 5 0 (Compound No.614) Compound of Example 203 12.5 1 5 5 5 0 (Compound No. 614) Compoundof Example 204 25 2 5 5 5 0 (Compound No. 618) Compound of Example 20412.5 2 5 5 5 0 (Compound No. 618) Compound of Example 205 25 1 5 5 5 0(Compound No. 621) Compound of Example 205 12.5 0 5 5 5 0 (Compound No.621) Compound of Example 212 25 2 5 5 5 0 (Compound No. 640) Compound ofExample 212 12.5 1 5 5 5 0 (Compound No. 640) Compound of Example 216 204 5 5 5 2 (Compound No. 658) Compound of Example 216 10 4 5 5 5 0(Compound No. 658) Compound of Example 217 20 4 5 5 5 0 (Compound No.659) Compound of Example 217 10 2 5 5 5 0 (Compound No. 659) Compound ofExample 218 20 1 5 5 5 0 (Compound No. 662) Compound of Example 218 10 05 5 5 0 (Compound No. 662) Compound of Example 219 20 4 5 5 — 0(Compound No. 663) Compound of Example 219 10 3 5 5 — 0 (Compound No.663) Compound of Example 232 20 4 5 4 5 0 (Compound No. 711) Compound ofExample 232 10 4 5 3 4 0 (Compound No. 711) Compound of Example 233 20 45 5 5 0 (Compound No. 712) Compound of Example 233 10 3 4 3 4 0(Compound No. 712) Compound of Example 234 25 0 5 4 5 0 (Compound No.716) Compound of Example 234 12.5 0 5 3 5 0 (Compound No. 716) Compoundof Example 235 20 3 5 5 5 0 (Compound No. 717) Compound of Example 23510 3 5 5 5 0 (Compound No. 717) Compound of Example 236 20 4 5 5 5 0(Compound No. 719) Compound of Example 236 10 3 5 5 5 0 (Compound No.719) Compound of Example 239 20 0 5 5 4 0 (Compound No. 732) Compound ofExample 240 25 3 5 4 5 0 (Compound No. 733) Compound of Example 240 12.52 5 3 5 0 (Compound No. 733) Compound of Example 241 20 3 5 4 5 0(Compound No. 735) Compound of Example 241 10 1 5 3 5 0 (Compound No.735) Compound of Example 242 25 4 5 4 5 0 (Compound No. 736) Compound ofExample 242 12.5 3 5 3 5 0 (Compound No. 736) Compound of Example 243 252 5 4 5 0 (Compound No. 737) Compound of Example 243 12.5 1 5 4 5 0(Compound No. 737) Compound of Example 245 20 4 5 5 5 0 (Compound No.740) Compound of Example 245 10 4 5 5 5 0 (Compound No. 740) Compound ofExample 248 10 3 5 — 5 0 (Compound No. 756) Compound of Example 248 5 15 — 5 0 (Compound No. 756) Compound of Example 249 20 3 5 5 5 3(Compound No. 758) Compound of Example 249 10 2 5 5 5 0 (Compound No.758) Compound of Example 250 20 4 5 5 5 0 (Compound No. 759) Compound ofExample 250 10 3 5 5 5 0 (Compound No. 759) Compound of Example 253 20 45 5 5 5 (Compound No. 762) Compound of Example 253 10 3 5 5 5 5(Compound No. 762) Compound of Example 255 20 5 5 4 5 2 (Compound No.778) Compound of Example 255 10 5 5 4 5 0 (Compound No. 778) Compound ofExample 256 20 4 5 5 5 3 (Compound No. 780) Compound of Example 256 10 35 5 5 2 (Compound No. 780) Compound of Example 258 10 3 5 — — 0(Compound No. 782) Compound of Example 260 20 3 5 5 5 0 (Compound No.802) Compound of Example 260 10 2 5 5 5 0 (Compound No. 802) Compound ofExample 261 20 2 5 5 5 0 (Compound No. 803) Compound of Example 261 10 25 4 5 0 (Compound No. 803) Compound of Example 267 20 2 5 5 5 0(Compound No. 845) Compound of Example 267 10 1 5 4 5 0 (Compound No.845) Compound of Example 268 25 1 5 5 5 1 (Compound No. 846) Compound ofExample 268 12.5 0 5 5 5 1 (Compound No. 846) Compound of Example 269 203 5 5 5 5 (Compound No. 850) Compound of Example 269 10 2 5 5 5 3(Compound No. 850) Compound of Example 271 25 2 5 4 4 1 (Compound No.894) Compound of Example 271 12.5 1 5 2 3 0 (Compound No. 894) Compoundof Example 272 20 0 5 5 4 0 (Compound No. 896) Compound of Example 27210 0 5 4 4 0 (Compound No. 896) Compound of Example 274 20 3 5 4 4 0(Compound No. 914) Compound of Example 274 10 3 5 3 4 0 (Compound No.914) Compound of Example 275 20 4 5 5 5 3 (Compound No. 931) Compound ofExample 275 10 4 5 5 5 1 (Compound No. 931) Compound of Example 276 20 45 4 5 0 (Compound No. 964) Compound of Example 276 10 3 5 3 5 0(Compound No. 964) Compound of Example 277 20 1 5 5 5 0 (Compound No.965) Compound of Example 277 10 0 5 — 5 0 (Compound No. 965) Compound ofExample 281 25 0 5 3 5 0 (Compound No. 998) Compound of Example 281 12.50 5 2 5 0 (Compound No. 998) Compound of Example 282 25 0 5 4 5 0(Compound No. 1000) Compound of Example 282 12.5 0 5 3 4 0 (Compound No.1000) Compound of Example 285 20 0 5 5 3 0 (Compound No. 1013) Compoundof Example 285 10 0 5 4 2 0 (Compound No. 1013) Compound of Example 28625 0 5 5 5 0 (Compound No. 1016) Compound of Example 286 12.5 0 5 5 5 0(Compound No. 1016) Compound of Example 287 25 0 5 5 3 0 (Compound No.1020) Compound of Example 287 12.5 0 5 5 1 0 (Compound No. 1020)Compound of Example 288 20 1 5 5 5 0 (Compound No. 1023) Compound ofExample 288 10 0 5 5 5 0 (Compound No. 1023) Compound of Example 289 250 5 5 5 0 (Compound No. 1027) Compound of Example 289 12.5 0 4 4 4 0(Compound No. 1027) Compound of Example 290 10 0 5 4 5 0 (Compound No.1040) Compound of Example 294 20 2 5 5 5 0 (Compound No. 1058) Compoundof Example 294 10 1 5 5 5 0 (Compound No. 1058) Compound of Example 29525 1 5 5 5 0 (Compound No. 1060) Compound of Example 295 12.5 0 5 5 5 0(Compound No. 1060) Compound of Example 296 20 2 5 5 5 0 (Compound No.1061) Compound of Example 296 10 1 5 5 5 0 (Compound No. 1061) Compoundof Example 303 25 1 4 4 5 0 (Compound No. 1083) Compound of Example 30312.5 0 3 3 5 0 (Compound No. 1083) Compound of Example 304 20 4 5 5 5 0(Compound No. 1086) Compound of Example 304 10 4 5 4 4 0 (Compound No.1086) Compound of Example 305 10 1 5 5 5 0 (Compound No. 1088) Compoundof Example 306 10 1 5 5 5 0 (Compound No. 1089) Compound of Example 30720 4 5 5 5 0 (Compound No. 1091) Compound of Example 307 10 3 5 5 5 0(Compound No. 1091) Compound of Example 308 20 4 5 5 5 0 (Compound No.1096) Compound of Example 308 10 2 5 4 5 0 (Compound No. 1096) Compoundof Example 309 20 5 5 5 5 5 (Compound No. 1099) Compound of Example 30910 4 5 5 5 2 (Compound No. 1099) Compound of Example 310 20 5 5 5 5 0(Compound No. 1100) Compound of Example 310 10 4 5 5 5 0 (Compound No.1100) Compound of Example 311 20 3 5 5 5 0 (Compound No. 1102) Compoundof Example 311 10 1 5 4 4 0 (Compound No. 1102) Compound of Example 31320 1 5 — — 0 (Compound No. 1115) Compound of Example 315 20 4 5 — 5 0(Compound No. 1119) Compound of Example 316 20 3 5 — — 0 (Compound No.1120) Compound of Example 316 10 2 5 — — 0 (Compound No. 1120) Compoundof Example 317 25 0 5 3 5 1 (Compound No. 1122) Compound of Example 31712.5 0 4 2 5 0 (Compound No. 1122) Compound of Example 318 20 1 5 5 5 0(Compound No. 1123) Compound of Example 318 10 0 5 5 5 0 (Compound No.1123) Compound of Example 319 20 3 5 5 5 0 (Compound No. 1124) Compoundof Example 319 10 2 5 5 5 0 (Compound No. 1124) Compound of Example 32025 2 5 5 5 0 (Compound No. 1125) Compound of Example 320 12.5 1 5 5 5 0(Compound No. 1125) Compound of Example 323 20 4 5 5 5 0 (Compound No.1140) Compound of Example 323 10 3 5 5 5 0 (Compound No. 1140) Compoundof Example 327 20 4 5 5 5 0 (Compound No. 1266) Compound of Example 32710 4 5 5 5 0 (Compound No. 1266) Compound of Example 328 20 4 5 5 5 0(Compound No. 1387) Compound of Example 328 10 3 3 3 5 0 (Compound No.1387) Compound of Example 329 20 4 5 5 5 0 (Compound No. 1391) Compoundof Example 329 10 2 5 5 5 0 (Compound No. 1391) Compound of Example 34520 4 5 5 5 0 (Compound No. 1658) Compound of Example 345 10 3 5 5 5 0(Compound No. 1658) Compound of Example 347 20 4 5 5 5 0 (Compound No.1710) Compound of Example 347 10 3 5 5 5 0 (Compound No. 1710) Compoundof Example 349 20 4 5 5 5 0 (Compound No. 1789) Compound of Example 34910 3 4 4 5 0 (Compound No. 1789) Compound of Example 352 20 4 5 5 — 0(Compound No. 1879) Compound of Example 356 20 3 5 5 5 0 (Compound No.1981) Compound of Example 356 10 2 4 3 5 0 (Compound No. 1981) Compoundof Example 357 20 3 5 5 5 0 (Compound No. 1985) Compound of Example 35710 2 5 5 5 0 (Compound No. 1985) Compound of Example 359 20 5 5 4 5 0(Compound No. 2038) Compound of Example 359 10 4 3 3 5 0 (Compound No.2038) Compound of Example 360 20 4 5 5 5 0 (Compound No. 2040) Compoundof Example 360 10 3 5 5 5 0 (Compound No. 2040) Compound of Example 36120 3 5 5 5 0 (Compound No. 2042) Compound of Example 361 10 2 5 5 4 0(Compound No. 2042) Compound of Example 365 20 3 5 5 5 0 (Compound No.2151) Compound of Example 365 10 2 5 4 5 0 (Compound No. 2151) Compoundof Example 394 20 3 5 5 5 0 (Compound No. 2289) Compound of Example 39410 2 5 4 5 0 (Compound No. 2289) Comparative compound 25 0 1 0 0 0

TEST EXAMPLE 2 Tests of Herbicidal Effects (Soil Treatment)

Upland soll was filled in 150 cm² pot, and seeds of barnyardgrass andindian mustard (Brassica juncea (L.) Czern. et Coss) were sowed, andgrown in a greenhouse. At the next day of seeding, a predeterminedchemical dosage of the wettable powder prepared in accordance withPreparation example 1 was diluted in water and applied to soil surface.After 21 days from the treatment, herbicidal effects were judged inaccordance with the judgment standard of Test example 1, and the resultswere shown in Table 3.

TABLE 3 Test of herbicidal effects Herbicidal effects Dosage Barnyard-indian Test compound (kg/a) grass mustard Example 23 2 4 5 (Compound No.806) Example 171 5 5 5 (Compound No. 506) Example 236 5 3 5 (CompoundNo. 719) Example 245 5 3 5 (Compound No. 740) Example 249 5 4 5(Compound No. 758) Example 256 5 3 5 (Compound No. 780) Example 309 5 55 (Compound No. 1099) Example 310 5 5 5 (Compound No. 1100)

TEST EXAMPLE 3 Test of Herbicidal Effects (Foliar Treatment)

Upland soil was filled in 150 cm² pot, and seeds of velvetleaf, tallmorningglory, indian mustard, black nightshade redroot pigweed weresowed, and grown in a greenhouse. After the weeds were grown with 10 to15 cm or so, a predetermined chemical dosage of the wettable powderprepared in accordance with Preparation example 1 was diluted with watercontaining 0.05% of GRAMIN-S and applied as a foliar treatment. After 14days from the treatment, herbicidal effects were judged in accordancewith the judgment standard of Test example 1, and the results were shownin Table 4. Incidentally, “-” in the table means no test was carriedout.

TABLE 4 Test of herbicidal effects Herbicidal effects Chemical Talldosage Velvet- Morning Indian Black Redroot Test compound (kg/a) leafglory mustard Nightshade pigweed Example 23 2 4 5 5 5 4 (Compound No.806) Example 236 0.5 — 4 3 — 3 (Compound No. 719)

TEST EXAMPLE 4 Tests of Herbicidal Effects and Crop Injury AgainstTransplanted Paddy-field Rice

Paddy filed soil was filled in 1/5000 are Wagner pot, seeds ofbarnyardgrass (Echinochloa oryzicola Vasing.), Scirpus joncoides andannual broad-leaved weeds (Lindernia spp. and Rotala indica) which areawaken from dormancy were mixed at the surface layer of 1 cm. Also,tubers of Cyperus serotinus, Sagittaria pygmaea and Eleocharis kuroguwaiwhich are awaken from dormancy were planted, and further seedlings ofpaddy-field ric at 2.2-leaf stage were transplantedand they were grownunder the flooded condition in a greenhouse. After 3 days from thetransplanting, a predetermined chemical dosage of the wettable powderprepared in accordance with Preparation example 5 was diluted withwater, and applied to the pot. After 25 days, herbicidal effects andcrop injury against transplanted paddy-field rice were judged accordingto the following judgment standard, and the results were shown in Table5. Incidentally, “-” in the table means a composition containing noeffective ingredient.

Judgment standard

-   0: Growth inhibition rate; 0 to 15%-   1: Growth inhibition rate; 16 to 35%-   2: Growth inhibition rate; 36 to 55%-   3: Growth inhibition rate; 56 to 75%-   4: Growth inhibition rate; 76 to 95%-   5: Growth inhibition rate; 96 to 100%.

TABLE 5 Tests of herbicidal effects and crop injury against transplantedpaddy-field rice Second herbi- cidally 3-phenoxy-4- active Crop injurypyridazinol com- Herbicidal effects against Test derivatives poundBarnyard Broad Scirpus Sagittaria Cyperus Eleocharis transplanted No.(g/a) (g/a) grass leaf joncoides pygmaea serotinus kuroguwai rice 1Example 1 (10) A(5) 5 5 5 5 5 5 0 2 Example 1 (5) A(5) 5 5 5 5 5 4 0 3Example 1 (10) B(5) 5 5 5 5 5 4 0 4 Example 1 (5) B(5) 5 5 5 5 5 4 0 5Example 1 (10) C(5) 5 5 5 5 5 4 0 6 Example 1 (5) C(5) 5 5 5 5 5 4 0 7Example 1 (10) — 4 4 4 4 5 0 0 8 Example 1 (5) — 2 3 2 4 4 0 0 9 Example6 (10) A(5) 5 5 5 5 5 5 0 10 Example 6 (5) A(5) 5 5 5 5 5 5 0 11 Example6 (10) C(5) 5 5 5 5 5 5 0 12 Example 6 (5) C(5) 5 5 5 5 5 5 0 13 Example6 (10) — 2 5 5 5 5 3 0 14 Example 6 (5) — 1 5 5 5 5 2 0 15 Example 16A(5) 5 5 5 5 5 2 0 (10) 16 Example 16 (5) A(5) 5 5 5 5 5 2 0 17 Example16 B(5) 5 5 5 5 5 3 0 (10) 18 Example 16 (5) B(5) 5 5 5 5 5 2 0 19Example 16 — 0 5 5 4 5 1 0 (10) 20 Example 16 (5) — 0 5 3 3 4 0 0 21Example 23 A(5) 5 5 5 5 5 5 0 (10) 22 Example 23 (5) A(5) 5 5 5 5 5 3 023 Example 23 B(5) 5 5 5 5 5 5 0 (10) 24 Example 23 (5) B(5) 5 5 5 5 5 30 25 Example 23 C(5) 5 5 5 5 5 5 0 (10) 26 Example 23 (5) C(5) 5 5 5 5 52 0 27 Example 23 — 3 5 5 5 5 3 0 (10) 28 Example 23 (5) — 2 5 5 5 5 2 029 Example 47 A(5) 5 5 5 5 5 5 0 (10) 30 Example 47 (5) A(5) 5 5 5 5 5 50 31 Example 47 — 3 5 5 5 5 2 0 (10) 32 Example 47 (5) — 3 5 4 5 5 1 033 Example 171 A(5) 5 5 5 5 5 4 0 (10) 34 Example 171 A(5) 5 5 5 5 5 4 0(5) 35 Example 171 B(5) 5 5 5 5 5 4 0 (10) 36 Example 171 B(5) 5 5 5 5 54 0 (5) 37 Example 171 C(5) 5 5 5 5 5 4 0 (10) 38 Example 171 C(5) 5 5 55 5 3 0 (5) 39 Example 171 — 3 5 5 5 5 3 0 (10) 40 Example 171 — 2 5 5 55 2 0 (5) 41 Example 191 A(5) 5 5 5 5 5 3 0 (2.5) 42 Example 191 B(5) 55 5 5 5 3 0 (2.5) 43 Example 191 C(5) 5 5 5 5 5 3 0 (2.5) 44 Example 191— 1 3 3 2 5 1 0 (2.5) 45 Example 245 A(5) 5 5 5 5 5 3 0 (10) 46 Example245 A(5) 5 5 5 5 5 2 0 (5) 47 Example 245 C(5) 5 5 5 5 5 3 0 (10) 48Example 245 C(5) 5 5 5 5 5 2 0 (5) 49 Example 245 — 4 5 5 5 5 1 0 (10)50 Example 245 — 3 5 5 4 4 0 0 (5) 51 Example 249 A(5) 5 5 5 5 5 3 0(10) 52 Example 249 A(5) 5 5 5 5 5 3 0 (5) 53 Example 249 — 2 5 5 5 5 20 (10) 54 Example 249 — 1 5 3 5 5 1 0 (5) 55 Example 288 A(5) 5 5 5 5 55 0 (10) 56 Example 288 A(5) 5 5 5 5 5 5 0 (5) 57 Example 288 — 0 5 5 55 3 0 (10) 58 Example 288 — 0 5 5 5 4 2 0 (5) 59 — A 5 5 4 5 4 2 0 (30)60 — A(5) 3 4 3 4 2 0 0 61 — B 5 5 4 5 4 2 0 (30) 62 — B(5) 3 4 3 4 2 00 63 — C 5 5 4 5 4 2 0 (30) 64 — C(5) 3 5 2 4 1 0 0

TEST EXAMPLE 5 Tests of Herbicidal Effects and Crop Injury AgainstUpland Crops (Soil Treatment)

Upland soil was filled in 150 cm² pot, and seeds of barnyardgrass,Cyperus esculentus L., velvetleaf, black nightshade, tall morninggloryand corn were sowed, and grown in a greenhouse. At the next day ofseeding, a predetermined chemical dosage of the wettable powder preparedin accordance with Preparation example 5 was diluted with water andapplied to soil surface. After 21 days from the treatment, herbicidaleffects and crop injury against corn were judged according to thefollowing judgment standard, and the results were shown in Tables 6 to8. Incidentally, “-” in the table means that the composition does notcontain the effective ingredient.

Judgment standard

-   0: Growth inhibition rate; 0 to 9%-   1: Growth inhibition rate; 10 to 19%-   2: Growth inhibition rate; 20 to 29%-   3: Growth inhibition rate; 30 to 39%-   4: Growth inhibition rate; 40 to 49%-   5: Growth inhibition rate; 50 to 59%-   6: Growth inhibition rate; 60 to 69%-   7: Growth inhibition rate; 70 to 79%-   8: Growth inhibition rate; 80 to 89%-   9: Growth inhibition rate; 90 to 98%-   10: Growth inhibition rate; 99 to 100%.

TABLE 6 Tests of herbicidal effects and crop injury against corn(Example 23 + compound D) Second 3-phenoxy- herbicidally Crop4-pyridazinol active Herbicidal effects injury Test derivatives compoundBarnyard- Tall Black against No. (g/ha) (g/ha) grass VelvetleafMorningglory Nightshade corn 1 Example 23 D(25) 10 10 9 10 0 (250) 2Example 23 D(25) 10 10 7 10 0 (125) 3 Example 23 D(25) 10 10 8 10 0 (63)4 — D(25) 10 9 5 9 0 5 Example 23 D(12.5) 10 10 9 10 0 (250) 6 Example23 D(12.5) 10 10 5 9 0 (125) 7 Example 23 D(12.5) 10 9 3 9 0 (63) 8 —D(12.5) 10 7 0 9 0 9 Example 23 D(6.3) 10 10 6 9 0 (250) 10 Example 23D(6.3) 9 10 5 10 0 (125) 11 Example 23 D(6.3) 5 9 1 9 0 (63) 12 — D(6.3)3 6 2 5 0

TABLE 7 Test of herbicidal effects and chemical damage against corn(Example 23 + compound E) 3-phenoxy- Second 4-pyrida- herbi- zinolcidally crop deriva- active Herbicidal effects injury Test tivescompound Barnyard- Cyperus Velvet- TallMorning Black against No. (g/ha)(g/ha) grass esculentus leaf glory Nightshade corn 1 Example 23 E(200)10 9 10 10 10 0 (125) 2 Example 23 E(200) 10 9 10 10 10 0 (63) 3 —E(200) 10 8 10 10 9 0 4 Example 23 E(100) 10 9 10 10 10 0 (125) 5Example 23 E(100) 10 8 10 10 9 0 (63) 6 — E(100) 9 8 7 7 6 0 7 Example23 E(50) 9 8 10 8 10 0 (125) 8 Example 23 E(50) 10 9 9 7 9 0 (63) 9 —E(50) 7 8 7 6 7 0

TABLE 8 Test of herbicidal effects and chemical damage against corn(Example 23 + compound F) 3- phenoxy- 4- Second pyrida- herbi- zinolcidally Crop deriva- active Herbicidal effects injury Test tivescompound Barnyard- Cyperus Tall Black against No. (g/ha) (g/ha) grassesculentus Velvetleaf Morningglory Nightshade corn 1 Example F(100) 10 910 9 10 0 23 (125) 2 Example F(100) 10 9 10 9 10 0 23 (63) 3 — F(100) 99 10 8 8 0 4 Example F(50) 10 9 10 7 10 0 23 (125) 5 Example F(50) 9 910 7 10 0 23 (63) 6 — F(50) 8 9 10 5 3 0 7 Example F(25) 9 9 10 7 9 0 23(125) 8 Example F(25) 7 8 9 5 10 0 23 (63) 9 — F(25) 4 8 9 2 6 0

TEST EXAMPLE 6 Tests of Herbicidal Effects and Crop Injury AgainstUpland crops (foliar treatment)

Upland soil was filled in 150 cm² pot, and seeds of barnyardgrass,Cyperus esculentus L., velvetleaf, black nightshade, tall morninggloryand corn were sowed, and grown in a greenhouse. After the weeds weregrown with 10 to 15 cm or so, a predetermined chemical dosage of thewettable powder prepared in accordance with Preparation example 5 wasdiluted with water containing 0.05% of GRAMIN S and applied as a foliartreatment. After 14 days from the treatment, herbicidal effects and cropinjury were judged in accordance with the judgment standard of Testexample 5, and the results were shown in Tables 9 and 10. Incedentally,“-” in the table means no effective ingredient was contained.

TABLE 9 Test of herbicidal effects and crop injury against corn (Example23 + compound E) 3-phenoxy- Second 4-pyrida- herbi- zinol cidally cropderiva- active Herbicidal effects injury Test tives compound BarnyardCyperus Velvet- TallMorning Black against No. (g/ha) (g/ha) grassesculentus leaf glory Nightshade corn 1 Example 23 E(200) 9 8 10 9 10 0(250) 2 Example 23 E(200) 9 9 10 9 10 0 (125) 3 Example 23 E(200) 9 9 108 10 0 (63) 4 — E(200) 7 8 10 9 10 0 5 Example 23 E(100) 9 9 10 9 10 0(250) 6 Example 23 E(100) 9 8 10 9 10 0 (125) 7 Example 23 E(100) 8 9 108 9 0 (63) 8 — E(100) 2 7 10 7 10 0 9 Example 23 E(50) 8 9 10 7 10 0(250) 10 Example 23 E(50) 5 8 10 9 10 0 (125) 11 Example 23 E(50) 2 8 108 10 0 (63) 12 — E(50) 1 6 9 6 9 0

TABLE 10 Test of herbicidal effects and crop injury against corn(Example 23 + compound F) Second herbi- 3-phenoxy-4- cidally Croppyridazinol active Herbicidal effects injury Test derivatives compoundBarnyard- Cyperus Velvet- TallMorning Black against No. (g/ha) (g/ha)grass esculentus leaf glory Nightshade corn 1 Example 23 F(100) 8 7 10 910 0 (250) 2 Example 23 F(100) 6 7 9 9 10 0 (125) 3 — F(100) 2 6 10 9 90 4 Example 23 F(50) 4 7 10 9 10 0 (250) 5 Example 23 F(50) 2 7 10 9 100 (125) 6 — F(50) 0 5 10 5 10 0 7 Example 23 F(25) 1 7 10 6 10 0 (250) 8Example 23 F(25) 1 6 10 5 10 0 (125) 9 — F(25) 0 4 9 2 7 0

Utilizability in Industry

The compounds of the present invention have herbicidal activities, andcan be used as a herbicidal composition for a paddy field, upland field,orchard, pasture, turf, forest or non-crop land.

The compounds of the present invention show herbicidal activitiesagainst various weeds which cause problems in a paddy field, forexample, annual broad-leaved weeds such as Lindernia spp., Vandelliaangustifolia Benth., Rotala indica, Elatine triandra, Monochoriavaginaris, Murdannia keisak, Dopatirum junceum (Roxb.) Hamilt, Ammanniamultiflora, etc.; perennial arrowhead weeds such as Sagittaria pygmaeaMiq., arrowhead (Sagittaria trifolia L.), Alisma canaliculatum, etc.;annual Cyperaceous weeds such as flatsedge, smallflower umbrellasedge,etc.; perennial Cyperaceous weeds such as needle spikerush, Scirpusjoncoides, Cyperus serotinus, Scrips Nipponicus Makino, etc.; or annualperennial Graminaceous weeds such as barnyardgrass, Leersia oryzoides(L.) Swartz., and the like, and show no crop injury against rice whichcauses any problem.

Also, the compounds of the present invention show herbicidal activitiesboth by foliar application and soil application agaist valious kinds ofweeds, which are troublesome in upland fields.

Moreover, they can be used not only in a paddy field and an uplandfiled, but also in an orchard, a mulberry field and a non-crop land.

Also, weeding spectrum of the herbicidal composition of the presentinvention can be enlarged by using 3-phenoxy-4-pyridazinol derivativesand a second herbicidally active compound in admixture which areeffective ingredients than its range to be applied which had beenobtained with a single agent use. The weeding spectrum of thecomposition according to the present invention covers Graminaceousweeds, annual broad-leaved weeds and whole perennial weeds such asArrowhead, Cyperaceous weeds, etc. Moreover, the composition of thepresent invention has high safety to paddy-field rice or upland crops,and has a wide application window. Also, the composition of the presentinvention shows synergistic effects in the herbicidal effects, and showssufficient effects with a mixture of compounds with a markedly lowerchemical dosage than the chemical dosage is used as a single agent inthe case where each. As a result, the composition of the presentinvention is hightened in herbicidal activity so that it is sufficientwith a one time treatment agent, and its effects are continued for along period of time. Also, the composition of the present inventionshows no crop injury against paddy-field rice, and it can be appliedboth of before transplanting and immediately after transplanting.

1. A compound represented by the formula:

wherein R¹ is a chlorine atom or a bromine atom, R² is a hydrogen atom,R³, R⁴, R⁵, R⁶ and R⁷ each independently represent a hydrogen atom, afluorine atom, a chlorine atom, a bromine atom, an iodine atom, a C₁ toC₄ alkyl group, a C₃ to C₄ cycloalkyl group, a cyano group, a C₂ to C₃alkoxycarbonyl group, a nitro group, a C₁ to C₃ alkoxy group or atrifluoromethoxy group, or R³, R⁴, R⁵, R⁶ and R⁷ are a group representedby —CH₂CH₂CH₂—, —CH(CH₃)CH₂CH₂—, OCH₂CH₂, —OCH═CH— or

which is formed by two adjacent members of R³, R⁴, R⁵, R⁶ and R⁷,provided that R³ is not a hydrogen atom, and m and n are both zero, asalt thereof or an ester thereof.
 2. The compound, a salt thereof or anester thereof according to claim 1, wherein R¹ is a chlorine atom. 3.The compound, a salt thereof or an ester thereof according to claim 1,wherein R³, R⁴, R⁵, R⁶ and R⁷ each independently represent a hydrogenatom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom,a C₁ to C₃ alkyl group, a C₃ to C₄ cycloalkyl group, a cyano group or aC₁ to C₂ alkoxy group, or R³, R⁴, R⁵, R⁶ and R⁷ are a group representedby —CH₂CH₂CH₂— or —OCH═CH—, which is formed by two adjacent members ofR³, R⁴, R⁵, R⁶ and R⁷, provided that R³ is not a hydrogen atom.
 4. Thecompound, a salt thereof or an ester thereof according to claim 1,wherein R¹ is a chlorine atom, R³, R⁴, R⁵, R⁶ and R⁷ each independentlyrepresent a hydrogen atom, a fluorine atom, a chlorine atom, a bromineatom, an iodine atom, a methyl group, an ethyl group, an isopropylgroup, a cyclopropyl group or a methoxy group, or R³, R⁴, R⁵, R⁶ and R⁷are a group represented by —CH₂CH₂CH₂—, which is formed by two adjacentmembers of R³, R⁴, R⁵, R⁶ and R⁷, provided that R³ is not a hydrogenatom.
 5. The compound according to claim 1, wherein the compound isselected from the group consisting of6-chloro-3-(2-iodophenoxy)-4-pyridazinol,6-chloro-3-(2-methyiphenoxy)-4-pyridazinol,6-chloro-3-(2-cyclopropyiphenoxy)-4-pyridazinol,6-chloro-3-(2,3-dihydro-1H-inden-4-yloxy)-4-pyridazinol,3-(1-benzofuran-7-yloxy)-6-chloro-4-pyridazinol,6-chloro-3-(2-methoxy-5-methylphenoxy)-4-pyridazinol,6-chloro-3-(2-chloro-6-cyclopropylphenoxy)-4-pyridazinol,3-(2-bromo-6-methylphenoxy)-6-chloro-4-pyridazinol,6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol and6-chloro-3-(2-cyclopropyl-3,5-dimethyiphenoxy)-4-pyridaziflol, or a saltthereof or an ester thereof.
 6. The ester of the compound according toclaims 1, 2, 3, 4 or 5, in which a group bonded to the oxygen atom ofthe hydroxyl group at the 4-position of the pyrazine ring is a C₂ to C₄alkylcarbonyl group; a benzoyl group which is unsubstituted orsubstituted with a methyl group or a4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxycarbonyl group; a1-azetidinylcarbonyl group; a 4-morpholinylcarbonyl group; a C₂ to C₃alkoxycarbonyl group which is unsubstituted or substituted with 1 to 3chlorine atoms; a dimethylcarbamoyl group; a methoxy(methyl)carbamoylgroup; a C₁ to C₃ alkylsulfonyl group which is unsubstituted orsubstituted with 1 to 3 fluorine atoms; or a phenylsulfonyl group whichis unsubstituted or substituted with a chlorine atom, a methyl group, a4-(2,4-dichlorobenzoyl)-1,3-dimethyl-1H-pyrazol-5-yloxysulfonyl group ora nitro group.
 7. The compound or a salt thereof or an ester thereofaccording to claim 1, wherein the compound is6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methylbenzoate.
 8. The compound or a salt thereof or an ester thereofaccording to claim 1, wherein the compound is6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyldimethylcarbamate.
 9. The compound or a salt thereof or an ester thereofaccording to claim 1, wherein the compound is6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-propanesulfonate.
 10. The compound or a salt thereof or an esterthereof according to claim 1, wherein the compound is6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-methylbenzenesulfonate.
 11. The compound or a salt thereof or an esterthereof according to claim 1, wherein the compound is6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl4-morpholinecarboxylate.
 12. The compound or a salt thereof or an esterthereof according to claim 1, wherein the compound is6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinyl1-azetizinecarboxylate.
 13. The compound or a salt thereof or an esterthereof according to claim 1, wherein the compound is6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinylbenzenesulfonate.
 14. An agricultural chemical composition whichcomprises the compound, a salt thereof or an ester thereof according toclaim 1 as an effective ingredient in combination with a carrier.
 15. Aherbicidal composition which comprises (i) a herbicidally effectiveamount of at least one 3-phenoxy-4-pyridazinol compound selected fromthe group consisting of the compound, a salt thereof or an ester thereofaccording to claim 1, and (ii) a herbicidally effective amount of atleast one herbicidally active compound selected from the groupconsisting of4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate,2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone,2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-4′-methylacetophenone,5-cyclopropyl-1,2-oxazol-4-yl α-α-α-trifluoro-2-mesyl-p-tolyl ketone,2-(2-chloro-4-mesylbenzoyl)cyclohexan-1,3-dione,2-(4-mesyl-2-nitrobenzoyl)cyclohexan-1,3-dione and4-chloro-2-(methylsulfonyl)phenyl 5-cyclopropyl-4-isoxazolyl ketone. 16.The herbicidal composition according to claim 15, wherein theherbicidally active compound is4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-p-toluenesulfonate. 17.A method for killing weeds comprising applying to weeds or a locusthereof a herbicidally effective amount of the compound, a salt thereofor an ester according to claim
 1. 18. A method for killing weedscomprising applying to weeds or a locus thereof a herbicidally effectiveamount of the composition according to claim 15.